1-phenylpyrrolidine-2-one-3-carboxamides

ABSTRACT

The invention relates to 1-phenylpyrrolidin-2-one-3-carboxamides of the formula I 
                         
where the variables R 1 , R 2 , R 3 , X, Y, A, n, R a , R b , R c , R d  and R e  are as defined in claim 1 and to their agriculturally useful salts.
 
     Moreover, the invention relates to
         the use of compounds I and/or their salts as herbicides;   crop protection compositions comprising at least one 1-phenylpyrrolidin-2-one-3-carboxamide of the formula I and/or at least one agriculturally useful salt of I as active substances; and also   a method for controlling unwanted vegetation, which comprises allowing a herbicidally effective amount of at least one 1-phenylpyrrolidin-2-one-3-carboxamide of the formula I or an agriculturally useful salt of I to act on plants, their habitat or on seed.

CROSS REFERENCE TO RELATED APPLICATION

This application is a 35 USC § 371 National Phase Entry Application fromPCT/EP2003/011557, filed Oct. 17, 2003, and designating the UnitedStates.

The present invention relates to 1-phenylpyrrolidin-2-one-3-carboxamidesand their agriculturally useful salts, to compositions comprising suchcompounds and to the use of the 1-phenylpyrrolidin-2-one-3-carboxamides,of their salts or of compositions comprising them as herbicides.

WO 95/33719 describes 1-arylthiazolidinones, 1-aryloxazolidinones and1-arylpyrrolidinones of the formula:

where A is an aromatic or heteroaromatic radical, n is 0 or 1, x is inparticular S, O or CH₂, Y is in particular S, O, CH₂ or CH(CH₃) or agroup NR⁶, Z is in particular NH or O, R¹ is preferably selected fromunsubstituted or substituted alkyl, alkenyl, alkynyl, unsubstituted orsubstituted cycloalkyl, unsubstituted or substituted phenyl, benzyl orhetaryl, acyl, alkoxycarbonylalkyl and silyl, R² and R³ are inparticular hydrogen and R⁶ is inter alia hydrogen, formyl, unsubstitutedor substituted alkyl, alkenyl, alkynyl, cycloalkyl or unsubstituted orsubstituted aryl.

WO 95/33718 describes 1-phenylpyrrolidinethiones having herbicidalactivity which, in the 3-position of the pyrrolidinethione ring, containa group O—C(O)—NR¹R² where R¹R² are, for example, hydrogen, anunsubstituted or substituted hydrocarbon radical or hetaryl, or togetherwith the nitrogen atom to which they are attached form a heterocycle.

Furthermore, U.S. Pat. No. 4,874,422 discloses herbicidally active1-phenylpyrrolidin-2-one-3-carboxamides of the formula A

where X is hydrogen or halogen, Y and Z independently of one another areO or S, n is 0 or 1, R¹ is hydrogen, alkyl, alkenyl, alkynyl,cycloalkyl, alkoxy, phenyl, halophenyl, benzyl, halobenzyl, or alkylwhich is substituted by alkoxy, alkylthio, phenyl, hydroxyl or cyano, R²is hydrogen or alkyl, R³ is alkyl or alkenyl and R⁴ is selected from thegroup consisting of hydrogen, halogen, methyl, trifluoromethyl,1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrafluoroethyloxy, difluoromethoxy,trifluoromethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl,methoxyiminomethyl, methoxyimino-1-ethyl, benzyloxyiminomethyl andbenzyloxyimino-1-ethyl.

The herbicidal activity of the 1-arylpyrrolidinones described in theprior art is not always satisfactory. Their selectivity for harmfulplants is unsatisfactory, too. In particular, even at low applicationrates, such herbicides tend to interfere with the generation ofchlorophyll even in crop plants, which is undesirable in principle andmay lead to yield losses.

It is an object of the present invention to provide novel herbicidallyactive compounds which allow a better targeted control of unwantedplants than the known herbicides. Advantageously, the novel herbicidesshould be highly active against harmful plants. Moreover, highcompatibility with crop plants is desirable. Moreover, the compoundsshould have no adverse effect on the chlorophyll synthesis in cropplants.

We have found that this object is achieved by1-phenylpyrrolidin-2-one-3-carboxamides of the formula I defined belowand their agriculturally useful salts:

where the variables R¹, R², R³, X, Y, A, n, R^(a), R^(b), R^(c), R^(d)and R^(e) are as defined below:

-   R¹ is hydrogen, OH, Cl, Br, C₁-C₆-alkyl, C₃-C₆-cycloalkyl,    C₃-C₆-alkenyl, C₃-C₆-alkynyl, C(O)R⁴ or OC(O)R⁴;-   R² and R³ independently of one another are hydrogen, C₁-C₁₀-alkyl,    C₃-C₁₀-cycloalkyl, C₇-C₁₀-polycycloalkyl, C₃-C₈-alkenyl,    C₃-C₁₀-alkynyl, C₅-C₁₀-cycloalkenyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,    phenyl or 3- to 7-membered heterocyclyl, where the 9 last-mentioned    groups may be unsubstituted, partially or fully halogenated and/or    contain 1, 2 or 3 radicals selected from the group consisting of OH,    CN, NO₂, COOH, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,    C₁-C₄-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylthio,    C₁-C₄-haloalkyl-thio, unsubstituted or substituted phenyl, COOR⁵,    NR⁶R⁷, C(O)NR⁸SO₂R¹³, C(O)NR⁸R⁹ and 3- to 7-membered heterocyclyl,    and each heterocyclyl may contain 1, 2 or 3 heteroatoms selected    from the group consisting of oxygen, nitrogen, sulfur, a group NR¹⁰    and a group SO₂, and, if appropriate, 1, 2 or 3 carbonyl groups    and/or thiocarbonyl groups as ring members; and/or may contain a    ring-fused phenyl ring which is unsubstituted or substituted; or    -   R² and R³ with the group N-(A)_(n) to which they are attached        form a saturated 3- to 7-membered heterocycle which, in addition        to the nitrogen atom, may contain 1, 2 or a further 3        heteroatoms selected from the group consisting of oxygen,        nitrogen, sulfur and a group NR¹⁰ and, if appropriate, 1, 2 or 3        carbonyl groups and/or thiocarbonyl groups as ring members;-   R^(a), R^(b), R^(c), R^(d) and R^(e) independently of one another    are hydrogen, OH, CN, NO₂, halogen, C₁-C₁₀-alkyl, C₃-C₆-cycloalkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,    C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio,    C₁-C₄-haloalkylthio, C(O)R⁴, COOR⁵, NR⁶R⁷, C(O)NR⁸R⁹, S(O)₂NR⁸R⁹,    S(O)R¹¹, S(O)₂R¹¹ or C₁-C₄-alkoxy-C₁-C₆-alkyl; or    -   two adjacent radicals R^(a) to R^(e) together with the atoms to        which they are attached form a 5-, 6- or 7-membered saturated or        unsaturated ring which may contain one or two heteroatoms        selected from the group consisting of nitrogen, oxygen, sulfur        and a group NR¹⁰ as ring-forming atom and/or may carry one, two,        three or four radicals selected from the group consisting of        halogen and C₁-C₄-alkyl;-   X, Y independently of one another are oxygen or sulfur;-   n is 0 or 1;-   A is O, S(O)_(k) or NR¹², where k is 0, 1 or 2;-   R⁴, R⁸, R⁹ independently of one another are hydrogen or C₁-C₄-alkyl;-   R⁵, R¹¹ are C₁-C₄-alkyl;-   R⁶, R⁷ independently of one another are hydrogen, C₁-C₆-alkyl,    C₃-C₆-alkenyl, C₃-C₆-alkynyl, C(O)R⁴, COOR⁵ or S(O)₂R¹¹;-   R¹⁰, R¹² independently of one another are hydrogen, C₁-C₆-alkyl,    C₃-C₆-alkenyl or C₃-C₆-alkynyl; and-   R¹³ is phenyl which is unsubstituted or carries 1, 2, 3 or 4    substituents, where the substituents are selected from the group    consisting of halogen, nitro, cyano, OH, alkyl, alkoxy, haloalkyl,    haloalkoxy, COOR⁵, NR⁶R⁷ and C(O)NR⁸R⁹.

Accordingly, the present invention relates to1-phenyl-pyrrolidin-2-one-3-carboxamides of the formula I and theiragriculturally useful salts.

Moreover, the present invention relates to

-   -   the use of compounds I and/or their salts as herbicides;    -   crop protection compositions comprising at least one        1-phenylpyrrolidin-2-one-3-carboxamide of the formula I and/or        at least one agriculturally useful salt of I as active        substances; and    -   methods for controlling unwanted vegetation, which comprises        allowing a herbicidally effective amount of at least one        1-phenylpyrrolidin-2-one-3-carboxamide of the formula I or an        agriculturally useful salt of I to act on plants, their habitat        or on seed.

Depending on the substitution pattern, the compounds of the formula Imay contain one or more centers of chirality, in which case they arepresent as mixtures of enantiomers or diastereomers. The inventionprovides both the pure enantiomers or diastereomers and their mixtures.The invention also provides tautomers of compounds of the formula I.

If R¹ represents hydrogen, the 1-phenylpyrrolidin-2-one-3-carboxamidesof the formula I according to the invention can be present in the formof their agriculturally useful salts. In general, agriculturally usefulsalts are the salts of those bases or cations which have no adverseeffect on the herbicidal action of the compounds I. Thus, suitable basicsalts are in particular the salts of the alkali metals, preferably ofsodium and potassium, of the alkaline earth metals, preferably ofcalcium, magnesium and barium, and of the transition metals, preferablyof manganese, copper, zinc and iron, and also ammonium salts where theammonium ion may, if desired, carry one to four C₁-C₄-alkylsubstituents, C₁-C₄-hydroxyalkyl substituents, C₁-C₄-alkoxy-C₁-C₄-alkylsubstituents and/or one phenyl or benzyl substituent, preferablydiisopropylammonium, tetramethylammonium, tetrabutylammonium,trimethylbenzylammonium, trimethyl-2-hydroxyethylammonium,bis(2-hydroxyethyl)methylammonium, tris(2-hydroxyethyl)ammonium,bis(2-hydroxyethyl)-dimethylammonium,tris(2-hydroxyethyl)methylammonium, furthermore phosphonium ions,sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxoniumions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

The organic moieties mentioned in the definition of the substituents R¹to R¹² or as radicals on heterocyclic rings are—like the termhalo—collective terms for individual listings of the individual groupmembers. All carbon chains, i.e. all alkyl, haloalkyl, cyanoalkyl,aminoalkyl, aminocarbonylalkyl, alkoxy, haloalkoxy, alkylthio,haloalkylthio, alkylsulfinyl, alkylsulfonyl, alkynyl and alkenylmoieties, may be straight-chain or branched. Halogenated substituentspreferably carry one to five identical or different halogen atoms. Theterm halo denotes in each case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

-   -   C₁-C₄-alkyl: for example methyl, ethyl, propyl, 1-methylethyl,        butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;    -   C₁-C₆-alkyl: C₁-C₄-alkyl as mentioned above and also, for        example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,        2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,        1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl,        3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl,        1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl,        2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,        2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl or        1-ethyl-3-methylpropyl;    -   C₁-C₁₀-alkyl: C₁-C₆-alkyl as mentioned above and also, for        example, n-heptyl, 2-heptyl, 2-methylhexyl, n-octyl,        1-methylheptyl, 2-ethylhexyl, n-nonyl, 2-nonyl, n-decyl,        2-decyl, 2-propylheptyl and the like;    -   C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which        is partially or fully substituted by fluorine, chlorine, bromine        and/or iodine, i.e., for example, chloromethyl, dichloromethyl,        trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,        chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,        2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,        2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,        2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,        2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,        3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,        2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,        2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,        3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl,        heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,        1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,        4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;        in particular difluoromethyl, trifluoromethyl;    -   C₁-C₆-haloalkyl: C₁-C₄-haloalkyl as mentioned above and also        5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl,        undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl,        6-iodohexyl or dodecafluorohexyl;    -   C₁-C₂-fluoroalkyl: C₁-C₂-alkyl which carries 1, 2, 3, 4 or 5        fluorine atoms, for example difluoromethyl, trifluoromethyl,        2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,        1,1,2,2-tetrafluoroethyl and pentafluoroethyl;    -   C₁-C₂-fluoroalkoxy: C₁-C₂-alkoxy which carries 1, 2, 3, 4 or 5        fluorine atoms, for example difluoromethoxy, trifluoromethoxy,        2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,        1,1,2,2-tetrafluoroethoxy and pentafluoroethoxy;    -   C₁-C₄-alkoxy: for example methoxy, ethoxy, n-propoxy,        1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or        1,1-dimethylethoxy;    -   C₁-C₆-alkoxy: C₁-C₄-alkoxy as mentioned above and also, for        example, pentoxy, 1-methylbutoxy, 2-methylbutoxy,        3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy,        2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy,        2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,        1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,        2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,        1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy,        1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or        1-ethyl-2-methylpropoxy;    -   C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, i.e., for example, OCH₂F, OCHF₂, OCF₃,        OCH₂Cl, OCH(Cl)₂, OC(Cl)₃, chlorofluoromethoxy,        dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy,        2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,        2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,        2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,        2,2,2-trichloroethoxy, OC₂F₅, 2-fluoropropoxy, 3-fluoropropoxy,        2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy,        3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy,        3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,        OCH₂—C₂F₅, OCF₂—C₂F₅, 1-(CH₂F)-2-fluoroethoxy,        1-(CH₂Cl)-2-chloroethoxy, 1-(CH₂Br)-2-bromoethoxy,        4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or        nonafluorobutoxy, preferably OCHF₂ or OCHF₃;    -   C₁-C₄-alkoxy-C₁-C₆-alkyl: C₁-C₆-alkyl which is substituted by        C₁-C₆-alkoxy—as mentioned above—, i.e., for example, CH₂—OCH₃,        CH₂—OC₂H₅, n-propoxymethyl, CH₂—OCH(CH₃) 2, n-butoxymethyl,        (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, CH₂—OC(CH₃)₃,        2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)ethyl,        2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl,        2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,        2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl,        2-(ethoxy)propyl, 2-(n-propoxy)propyl, 2-(1-methylethoxy)propyl,        2-(n-butoxy)propyl, 2-(1-methylpropoxy)propyl,        2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl,        3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(n-propoxy)propyl,        3-(1-methylethoxy)propyl, 3-(n-butoxy)propyl,        3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,        3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,        2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl,        2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,        2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,        3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(n-butoxy)butyl,        3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,        3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,        4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl,        4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl,        4-(1,1-dimethylethoxy)butyl, 2-(1-methylethoxy)pentyl,        2-(n-butoxy)pentyl, 2-(1-methylpropoxy)pentyl,        2-(2-methylpropoxy)pentyl, 2-(1,1-dimethylethoxy)pentyl,        3-(methoxy)pentyl, 3-(ethoxy)pentyl, 3-(n-propoxy)pentyl,        3-(1-methylethoxy)pentyl, 3-(n-butoxy)pentyl,        3-(1-methylpropoxy)pentyl, 3-(2-methylpropoxy)pentyl,        3-(1,1-dimethylethoxy)pentyl, 4-(methoxy)pentyl,        4-(ethoxy)pentyl, 4-(n-propoxy)pentyl, 4-(1-methylethoxy)pentyl,        4-(n-butoxy)pentyl, 4-(1-methylpropoxy)pentyl,        4-(2-methylpropoxy)pentyl, 4-(1,1-dimethylethoxy)pentyl,        4-(methoxy)pentyl, 5-(ethoxy)pentyl, 5-(n-propoxy)pentyl,        5-(1-methylethoxy)pentyl, 5-(n-butoxy)pentyl,        5-(1-methylpropoxy)pentyl, 5-(2-methylpropoxy)pentyl,        5-(1,1-dimethylethoxy)pentyl, 2-(1-methylethoxy)hexyl,        2-(n-butoxy)hexyl, 2-(1-methylpropoxy)hexyl,        2-(2-methylpropoxy)hexyl, 2-(1,1-dimethylethoxy)hexyl,        3-(methoxy)hexyl, 3-(ethoxy)hexyl, 3-(n-propoxy)hexyl,        3-(1-methylethoxy)hexyl, 3-(n-butoxy)hexyl,        3-(1-methylpropoxy)hexyl, 3-(2-methylpropoxy)hexyl        3-(1,1-dimethylethoxy)hexyl, 4-(methoxy)hexyl, 4-(ethoxy)hexyl,        4-(n-propoxy)hexyl, 4-(1-methylethoxy)hexyl, 4-(n-butoxy)hexyl,        4-(1-methylpropoxy)hexyl, 4-(2-methylpropoxy)hexyl,        4-(1,1-dimethylethoxy)hexyl, 4-(methoxy)hexyl, 5-(ethoxy)hexyl,        5-(n-propoxy)hexyl, 5-(1-methylethoxy)hexyl, 5-(n-butoxy)hexyl,        5-(1-methylpropoxy)hexyl, 5-(2-methylpropoxy)hexyl,        5-(1,1-dimethylethoxy)hexyl, 6-(ethoxy)hexyl,        6-(n-propoxy)hexyl, 6-(1-methylethoxy)hexyl, 6-(n-butoxy)hexyl,        6-(1-methylpropoxy)hexyl, 6-(2-methylpropoxy)hexyl,        6-(1,1-dimethylethoxy)hexyl;    -   C₁-C₄-alkylthio: an alkylsulfanyl radical having 1 to 4 carbon        atoms, for example SCH₃, SC₂H₅, SCH₂—C₂H₅, SCH(CH₃)₂,        n-butylthio, SCH(CH₃)—C₂H₅, SCH₂—CH(CH₃) 2 or SC(CH₃) 3;    -   C₁-C₆-alkylthio: C₁-C₄-alkylthio as mentioned above and also,        for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio,        3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio,        hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio,        1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio,        4-methylpentylthio, 1,1-dimethylbutylthio,        1,2-dimethylbutylthio, 1,3-dimethylbutylthio,        2,2-dimethylbutylthio, 2,3-dimethylbutylthio,        3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,        1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,        1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;    -   C₁-C₄-haloalkylthio: a C₁-C₄-alkylthio radical as mentioned        above which is partially or fully substituted by fluorine,        chlorine, bromine and/or iodine, i.e., for example,        fluoromethylthio, difluoromethylthio, trifluoromethylthio,        chlorodifluoromethylthio, bromodifluoromethylthio,        2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio,        2-iodoethylthio, 2,2-difluoroethylthio,        2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio,        2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,        2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio,        2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio,        3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio,        2,2-difluoropropylthio, 2,3-difluoropropylthio,        2,3-dichloropropylthio, 3,3,3-trifluoropropylthio,        3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio,        heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio,        1-(chloromethyl)-2-chloroethylthio,        1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio,        4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio;    -   phenyl-C₁-C₄-alkyl: for example benzyl, 1-phenylethyl,        2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl,        3-phenylprop-1-yl, 1-phenylbut-1-yl, 2-phenylbut-1-yl,        3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl,        2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl,        1-(benzyl)eth-1-yl, 1-(benzyl)-1-(methyl)eth-1-yl or        1-(benzyl)prop-1-yl;    -   C₂-C₆-alkenyl: a monounsaturated aliphatic hydrocarbon radical        having 2 to 6 and in particular 2 to 4 carbon atoms, for example        ethenyl, prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl,        buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl,        2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl,        2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl,        penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl,        3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl,        2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,        1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,        3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl,        1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl,        1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl,        hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl,        1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl,        3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl,        1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl,        3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl,        1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,        3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl,        1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl,        3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,        1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,        1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl,        1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl,        1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,        2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl,        2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl,        3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl,        1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl,        1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl,        2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,        1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl,        1-ethyl-2-methylprop-1-en-1-yl and        1-ethyl-2-methylprop-2-en-1-yl;    -   C₃-C₈-alkenyl: an aliphatic hydrocarbon radical which contains a        C═C double bond and has 3 to 8, preferably 3 to 6 and in        particular 3 or 4 carbon atoms as mentioned above, which is        preferably not attached via a carbon atom of the double bond,        for example one of the radicals mentioned under C₂-C₆-alkenyl        and also 1-hepten-3-yl, 1-hepten-4-yl, 1-hepten-5-yl,        1-hepten-6-yl, 1-hepten-7-yl, 3-hepten-1-yl, 2-hepten-4-yl,        3-hepten-5-yl, 3-hepten-6-yl, 3-hepten-7-yl, 1-octen-3-yl,        1-octen-4-yl, 1-octen-5-yl, 1-octen-6-yl, 1-octen-7-yl,        1-octen-8-yl, 3-octen-1-yl, 2-octen-1-yl, 2-octen-4-yl,        3-octen-5-yl, 3-octen-6-yl, 3-octen-7-yl, 3-octen-8-yl and the        like;    -   C₂-C₆-haloalkenyl: C₂-C₆-alkenyl as mentioned above which is        partially or fully substituted by fluorine, chlorine, and/or        bromine, i.e., for example, 2-chlorovinyl, 2-chloroallyl,        3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl,        2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl,        3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl,        2,3,3-tribromoallyl and 2,3-dibromobut-2-enyl;    -   C₂-C₆-alkynyl: an aliphatic hydrocarbon radical which contains a        C—C triple bond and has 2 to 6 and in particular 2 to 4 carbon        atoms: for example ethynyl, propargyl (2-propynyl), 1-propynyl,        but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-3-yl,        pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl,        pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl,        hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl,        hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl,        hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-3-yl,        3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl,        4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl;    -   C₃-C₁₀-alkynyl: an aliphatic hydrocarbon radical which contains        a triple bond and has 3 to 10, preferably 3 to 6 and in        particular 3 or 4 carbon atoms as mentioned above, which is        preferably not attached via a carbon atom of the triple bond,        for example one of the radicals mentioned under C₂-C₆-alkynyl        and also 1-heptyn-3-yl, 1-heptyn-4-yl, 1-heptyn-5-yl,        1-heptyn-6-yl, 1-heptyn-7-yl, 3-heptyn-1-yl, 2-heptyn-4-yl,        3-heptyn-5-yl, 3-heptyn-6-yl, 3-heptyn-7-yl, 1-octyn-3-yl,        1-octyn-4-yl, 1-octyn-5-yl, 1-octyn-6-yl, 1-octyn-7-yl,        1-octyn-8-yl, 3-octyn-1-yl, 2-octyn-1-yl, 2-octyn-4-yl,        3-octyn-5-yl, 3-octyn-6-yl, 3-octyn-7-yl, 3-octyn-8-yl and the        like;    -   C₃-C₁₀-cycloalkyl: a monocyclic hydrocarbon radical having 3 to        10 carbon atoms, in particular 3 to 8 carbon atoms and        especially 3 to 6 carbon atoms, for example cyclopropyl,        cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl;    -   C₇-C₁₀-polycycloalkyl: a bicyclic, tricyclic or tetracyclic        hydrocarbon radical having 7 to 10 carbon atoms, for example        bicyclo[2.2.1]-hept-1-yl, bicyclo[2.2.1]hept-2-yl,        bicyclo[2.2.1]hept-7-yl, bicyclo[2.2.2]oct-1-yl,        bicyclo[2.2.2]oct-2-yl or adamantan-1-yl;    -   C₃-C₈-cycloalkyl-C₁-C₄-alkyl: C₁-C₄-alkyl which carries a        C₃-C₈-cycloalkyl radical as defined above, for example        cyclopropylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl,        1-cyclopropylprop-1-yl, 2-cyclopropylprop-1-yl,        3-cyclopropylprop-1-yl, 1-cyclopropylbut-1-yl,        2-cyclopropylbut-1-yl, 3-cyclopropylbut-1-yl,        4-cyclopropylbut-1-yl, 1-cyclopropylbut-2-yl,        2-cyclopropylbut-2-yl, 3-cyclopropylbut-2-yl,        3-cyclopropylbut-2-yl, 4-cyclopropylbut-2-yl,        1-(cyclopropylmethyl)eth-1-yl,        1-(cyclopropylmethyl)-1-(methyl)eth-1-yl,        1-(cyclopropylmethyl)prop-1-yl, cyclobutylmethyl,        1-cyclobutylethyl, 2-cyclobutylethyl, 1-cyclobutylprop-1-yl,        2-cyclobutylprop-1-yl, 3-cyclobutylprop-1-yl,        1-cyclobutylbut-1-yl, 2-cyclobutylbut-1-yl,        3-cyclobutylbut-1-yl, 4-cyclobutylbut-1-yl,        1-cyclobutylbut-2-yl, 2-cyclobutylbut-2-yl,        3-cyclobutylbut-2-yl, 4-cyclobutylbut-2-yl,        1-(cyclobutylmethyl)eth-1-yl,        1-(cyclobutylmethyl)-1-(methyl)eth-1-yl,        1-(cyclobutylmethyl)prop-1-yl, cyclopentylmethyl,        1-cyclopentylethyl, 2-cyclopentylethyl, 1-cyclopentylprop-1-yl,        2-cyclopentylprop-1-yl, 3-cyclopentylprop-1-yl,        1-cyclopentylbut-1-yl, 2-cyclopentylbut-1-yl,        3-cyclopentylbut-1-yl, 4-cyclopentylbut-1-yl,        1-cyclopentylbut-2-yl, 2-cyclopentylbut-2-yl,        3-cyclopentylbut-2-yl, 3-cyclopentylbut-2-yl,        4-cyclopentylbut-2-yl, 1-(cyclopentylmethyl)eth-1-yl,        1-(cyclopentylmethyl)-1-(methyl)eth-1-yl,        1-(cyclopentylmethyl)prop-1-yl, cyclohexylmethyl,        1-cyclohexylethyl, 2-cyclohexylethyl, 1-cyclohexylprop-1-yl,        2-cyclohexylprop-1-yl, 3-cyclohexylprop-1-yl,        1-cyclohexylbut-1-yl, 2-cyclohexylbut-1-yl,        3-cyclohexylbut-1-yl, 4-cyclohexylbut-1-yl,        1-cyclohexylbut-2-yl, 2-cyclohexylbut-2-yl,        3-cyclohexylbut-2-yl, 4-cyclohexylbut-2-yl,        1-(cyclohexylmethyl)eth-1-yl,        1-(cyclohexylmethyl)-1-(methyl)eth-1-yl,        1-(cyclohexylmethyl)prop-1-yl, cycloheptylmethyl,        1-cycloheptylethyl, 2-cycloheptylethyl, 1-cycloheptylprop-1-yl,        2-cycloheptylprop-1-yl, 3-cycloheptylprop-1-yl,        1-cycloheptylbut-1-yl, 2-cycloheptylbut-1-yl,        3-cycloheptylbut-1-yl, 4-cycloheptylbut-1-yl,        1-cycloheptylbut-2-yl, 2-cycloheptylbut-2-yl,        3-cycloheptylbut-2-yl, 4-cycloheptylbut-2-yl,        1-(cycloheptylmethyl)eth-1-yl,        1-(cycloheptylmethyl)-1-(methyl)eth-1-yl,        1-(cycloheptylmethyl)prop-1-yl, cyclooctylmethyl,        1-cyclooctylethyl, 2-cyclooctylethyl, 1-cyclooctylprop-1-yl,        2-cyclooctylprop-1-yl, 3-cyclooctylprop-1-yl,        1-cyclooctylbut-1-yl, 2-cyclooctylbut-1-yl,        3-cyclooctylbut-1-yl, 4-cyclooctylbut-1-yl,        1-cyclooctylbut-2-yl, 2-cyclooctylbut-2-yl,        3-cyclooctylbut-2-yl, 4-cyclooctylbut-2-yl,        1-(cyclooctylmethyl)eth-1-yl,        1-(cyclooctylmethyl)-1-(methyl)eth-1-yl or        1-(cyclooctylmethyl)prop-1-yl, preferably cyclopropylmethyl,        cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl.

C₅-C₁₀-cycloalkenyl: a mono- or bicyclic hydrocarbon radical having 5 to10 carbon atoms, in particular 5 to 8 carbon atoms and especially 5 to 6carbon atoms and which contains a C═C double bond, for examplecyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl,cyclohexen-4-yl, cyclohepten-1-yl, cyclohepten-3-yl, cyclohepten-4-yl,cycloocten-1-yl, cycloocten-3-yl, cycloocten-4-yl, cycloocten-5-yl,bicyclo[2.2.1]hept-2-en-1-yl, bicyclo[2.2.1]hept-2-en-2-yl,bicyclo[2.2.1]hept-2-en-5-yl, bicyclo[2.2.1]hept-2-en-7-yl,bicyclo[2.2.2]oct-2-en-1-yl, bicyclo[2.2.2]oct-2-en-2-yl,bicyclo[2.2.2]oct-2-en-5-yl, bicyclo[2.2.2]oct-2-en-7-yl;

-   -   unsubstituted or substituted phenyl: a phenyl group which is        unsubstituted or carries 1, 2, 3 or 4 substituents, where the        substituents are selected from the group consisting of halogen,        nitro, cyano, OH, alkyl, alkoxy, haloalkyl, haloalkoxy, COOR⁵,        NR⁶R⁷, C(O)NR⁸R⁹;    -   3- to 7-membered heterocyclyl: a heterocyclic radical which has        3, 4, 5, 6 or 7 ring members, where 1, 2 or 3 of the ring        members are heteroatoms selected from the group consisting of        oxygen, nitrogen, sulfur, a group SO₂ and a group NR¹⁰.        Moreover, the heterocycle may optionally contain 1, 2 or 3        carbonyl groups and/or thiocarbonyl groups as ring members. The        heterocycle may furthermore contain a ring-fused unsubstituted        or substituted phenyl ring. The heterocycle may be aromatic        (heteroaryl) or partially or fully saturated.    -   Examples of saturated heterocycles are: oxiran-1-yl,        aziridin-1-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl,        thietan-3-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl,        tetrahydrofuran-2-yl, tetrahydrofuran-3-yl,        tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl,        pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl,        1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl,        1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-oxazolidin-2-yl,        1,3-oxazolidin-3-yl, 1,3-oxazolidin-4-yl, 1,3-oxazolidin-5-yl,        1,2-oxazolidin-2-yl, 1,2-oxazolidin-3-yl, 1,2-oxazolidin-4-yl,        1,2-oxazolidin-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl,        pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-5-yl,        tetrahydropyrazol-1-yl, tetrahydropyrazol-3-yl,        tetrahydropyrazol-4-yl, tetrahydropyran-2-yl,        tetrahydropyran-3-yl, tetrahydropyran-4-yl,        tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl,        tetrahydropyran-4-yl, piperidin-1-yl, piperidin-2-yl,        piperidin-3-yl, piperidin-4-yl, 1,3-dioxan-2-yl,        1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl,        1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl,        1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl,        morpholin-2-yl, morpholin-3-yl, morpholin-4-yl,        hexahydropyridazin-1-yl, hexahydropyridazin-3-yl,        hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl,        hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl,        hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl,        piperazin-3-yl, hexahydro-1,3,5-triazin-1-yl,        hexahydro-1,3,5-triazin-2-yl, oxepan-2-yl, oxepan-3-yl,        oxepan-4-yl, thiepan-2-yl, thiepan-3-yl, thiepan-4-yl,        1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1,3-dioxepan-5-yl,        1,3-dioxepan-6-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-4-yl,        1,3-dithiepan-5-yl, 1,3-dithiepan-6-yl, 1,4-dioxepan-2-yl,        1,4-dioxepan-7-yl, hexahydroazepin-1-yl, hexahydroazepin-2-yl,        hexahydroazepin-3-yl, hexahydroazepin-4-yl,        hexahydro-1,3-diazepin-1-yl, hexahydro-1,3-diazepin-2-yl,        hexahydro-1,3-diazepin-4-yl, hexahydro-1,4-diazepin-1-yl and        hexahydro-1,4-diazepin-2-yl;    -   Examples of unsaturated heterocycles are:    -   dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl,        1,3-oxazolin-2-yl;    -   Examples of aromatic heterocyclyl are the 5- and 6-membered        aromatic, heterocyclic radicals, for example furyl, such as        2-furyl and 3-furyl, thienyl, such as 2-thienyl and 3-thienyl,        pyrrolyl, such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl, such as        3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl, such        as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl,        such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl, such        as 2-oxazolyl, 4-oxazolyl and 5-oxazolyl, thiazolyl, such as        2-thiazolyl, 4-thiazolyl and 5-thiazolyl, imidazolyl, such as        2-imidazolyl and 4-imidazolyl, oxadiazolyl, such as        1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and        1,3,4-oxadiazol-2-yl, thiadiazolyl, such as        1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl and        1,3,4-thiadiazol-2-yl, triazolyl, such as 1,2,4-triazol-1-yl,        1,2,4-triazol-3-yl and 1,2,4-triazol-4-yl, pyridinyl, such as        2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl, such as        3-pyridazinyl and 4-pyridazinyl, pyrimidinyl, such as        2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, furthermore        2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, in        particular pyridyl, pyrimidyl, furanyl and thienyl.

If the radicals R² and R³ together with the nitrogen atom to which theyare attached form a saturated heterocycle, n is preferably 0. In thiscase, the saturated heterocycle is selected, for example, from the groupconsisting of 1,3-oxazolidin-3-yl, 1,2-oxazolidin-2-yl, pyrrolidin-1-yl,pyrrolidin-2-on-1-yl, tetrahydropyrazol-1-yl,2-methyltetrahydropyrazol-1-yl, piperidin-1-yl, piperidin-2-on-1-yl,morpholin-4-yl, hexahydropyrimidin-1-yl, piperazin-1-yl,4-methylpiperazin-1-yl, hexahydro-1,3,5-triazin-1-yl,3,5-dimethyltriazin-1-yl, hexahydroazepin-1-yl,hexahydroazepin-2-on-1-yl, hexahydro-1,3-diazepin-1-yl,hexahydro-1,4-diazepin-1-yl, in particular from the group consisting ofpyrrolidin-1-yl, piperidin-1-yl and morpholin-4-yl.

If two adjacent radicals R^(a) to R^(e) together with the atoms to whichthey are attached form a 5-, 6- or 7-membered saturated or unsaturatedring which may contain one or two heteroatoms selected from the groupconsisting of nitrogen, oxygen, sulfur and a group NR¹⁰ as ring-formingatom(s) and/or may carry one, two, three or four radicals selected fromthe group consisting of halogen and C₁-C₄-alkyl, two adjacent radicalsR^(a) to R^(e), for example R^(b) and R^(c) or R^(c) and R^(d), togetherare a 3-, 4- or 5-membered saturated or unsaturated carbon chain inwhich one or two non-adjacent carbon atoms of the chain may be replacedby heteroatoms selected from the group consisting of O, N, a group NR¹⁰and S and in which the carbon atoms of the chain may carry one, two,three or four substituents selected from the group consisting of halogenand C₁-C₄-alkyl. For example, two adjacent radicals R^(a) to R^(e) maybe a chain of the formula —O—CH₂—O—, —O—(CH₂)₂—O—, —O—(CH₂)₂—,—O—(CH₂)₃—, —(CH₂)₃—, —(CH₂)₄— or —(CH₂)₅—

With a view to the use of the compounds of the formula I according tothe invention as herbicides, the variables R¹, R², R³, X, Y, A, n,R^(a), R^(b), R^(c), R^(d) and R^(e) are preferably as defined below,independently of one another and in particular in combination:

-   R¹ is hydrogen, OH, Cl, Br, C₁-C₆-alkyl or OC(O)R⁴, particularly    preferably hydrogen;-   R² is C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl,    C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenyl or    C₃-C₈-cycloalkyl-C₁-C₄-alkyl, where C₁-C₁₀-alkyl and    C₃-C₈-cycloalkyl may be partially or fully halogenated and/or may    carry one or two radicals selected from the group consisting of    C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio,    C₁-C₄-haloalkylthio, unsubstituted or substituted phenyl, COOR⁵,    NR⁶R⁷, C(O)NR⁸R⁹, phenyl which may be unsubstituted or substituted    by 1, 2 or 3 substituents selected from the group consisting of    halogen, nitro, OH, CN, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₆-alkylthio, C₁-C₄-haloalkylthio, unsubstituted or substituted    phenyl, COOR⁵, NR⁶R⁷, C(O)NR⁸R⁹. In particular, R² is C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₅-C₆-cycloalkenyl,    C₃-C₆-cycloalkyl-C₁-C₄-alkyl or unsubstituted or substituted phenyl,    where C₁-C₆-alkyl and C₃-C₆-cycloalkyl may be partially or fully    halogenated and/or may carry one or two, in particular one, radical    selected from the group consisting of C₁-C₆-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio,    unsubstituted or substituted phenyl, COOR⁵, NR⁶R⁷, C(O)NR⁸R⁹.    Particularly preferably, R² is C₁-C₆-alkyl, C₃-C₈-cycloalkyl,    unsubstituted or substituted phenyl, phenylalkyl or    C₃-C₈-cycloalkyl-C₁-C₄-alkyl;-   R³ is hydrogen or C₁-C₆-alkyl;-   X is oxygen;-   Y is oxygen; and-   A if present, is oxygen, a group N—R¹², where R¹²=hydrogen or alkyl,    or a group SO₂;-   n is 0;-   R^(a), R^(b), R^(c), R^(d), R^(e) are hydrogen, halogen, CN,    C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, in    particular halogen, CN, C₁-C₄-alkyl, C₁-C₂-fluoroalkyl and    C₁-C₂-fluoroalkoxy and especially fluorine, chlorine, bromine, CN,    C₁-C₄-alkyl, methoxy, CF₃, CHF₂, OCF₃ and OCHF₂.

With a view to the use as herbicides, preference is given to1-phenylpyrrolidin-2-one-3-carboxamides of the formula I according tothe invention where not more than 3 of the radicals R^(a), R^(b), R^(c),R^(d) and R^(e) and in particular 3 or 4 of the abovementioned radicalsare different from hydrogen. Particular preference is given to1-phenylpyrrolidin-2-one-3-carboxamides of the formula I where at leastR^(b) and/or R^(d) are different from hydrogen. In this case, the otherradicals R^(a)-R^(e), at least one of the radicals R^(a) and R^(e) andespecially both radicals R^(a) and R^(e) are particularly preferablyhydrogen. Particular preference is also given to compounds of theformula I in which R^(b) and R^(c) or R^(d) and R^(c) are different fromhydrogen and the other radicals of the radicals R^(a)-R^(e) arehydrogen. Another preferred embodiment of the invention relates tocompounds in which the radicals R^(a) and R^(e) or R^(a) and R^(b) orR^(a) and R^(c) are different from hydrogen and the other radicals ofthe radicals R^(a)-R^(e) are hydrogen.

Preferred radicals R^(a), R^(b), R^(c), R^(d), R^(e) are, in addition tohydrogen, the substituents halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, in particular halogen, CN, C₁-C₄-alkyl,C₁-C₂-fluoroalkyl and C₁-C₂-fluoroalkoxy and especially fluorine,chlorine, bromine, CN, C₁-C₄-alkyl, methoxy, CF₃, CHF₂, OCF₃ and OCHF₂.

A particularly preferred group of compounds of the formula I are thosecompounds in which R^(a) and R^(e) are hydrogen. Here, the radical

denotes, for example, a group of the formulae Q1 to Q31:

Another preferred group of compounds of the formula I are thosecompounds in which R^(a) and, if appropriate, one of the radicals R^(b),R^(c) or R^(e) are different from hydrogen and the other radicalsR^(a)-R^(e) are hydrogen. Here, the radical

denotes, for example, a group of the formulae Q32 to Q39:

Particular preference is given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ia (≡I whereR^(a)═R^(b)═H, X═O, Y═O, R¹═H, R³═CH₃ and n=0) where R^(b), R^(c), R^(d)and R² have the meanings mentioned above, in particular the meaningsmentioned as being preferred. Examples of such compounds are thecompounds Ia.1 to Ia.1717 in which the variables R^(b), R^(c), R^(d) andR² together have the meanings given in one row of Table 1.

TABLE 1 (Ia)

No. R^(b) R^(c) R^(d) R² 1. Cl H H H 2. Br H H H 3. F H H H 4. CH₃ H H H5. C₂H₅ H H H 6. CH(CH₃)₂ H H H 7. OCH₃ H H H 8. CN H H H 9. CF₃ H H H10. OCF₃ H H H 11. OCHF₂ H H H 12. Cl H H CH₃ 13. Br H H CH₃ 14. F H HCH₃ 15. CH₃ H H CH₃ 16. C₂H₅ H H CH₃ 17. CH(CH₃)₂ H H CH₃ 18. OCH₃ H HCH₃ 19. CN H H CH₃ 20. CF₃ H H CH₃ 21. OCF₃ H H CH₃ 22. OCHF₂ H H CH₃23. Cl H H C₂H₅ 24. Br H H C₂H₅ 25. F H H C₂H₅ 26. CH₃ H H C₂H₅ 27. C₂H₅H H C₂H₅ 28. CH(CH₃)₂ H H C₂H₅ 29. OCH₃ H H C₂H₅ 30. CN H H C₂H₅ 31. CF₃H H C₂H₅ 32. OCF₃ H H C₂H₅ 33. OCHF₂ H H C₂H₅ 34. Cl H H n-C₃H₇ 35. Br HH n-C₃H₇ 36. F H H n-C₃H₇ 37. CH₃ H H n-C₃H₇ 38. C₂H₅ H H n-C₃H₇ 39.CH(CH₃)₂ H H n-C₃H₇ 40. OCH₃ H H n-C₃H₇ 41. CN H H n-C₃H₇ 42. CF₃ H Hn-C₃H₇ 43. OCF₃ H H n-C₃H₇ 44. OCHF₂ H H n-C₃H₇ 45. Cl H H CH(CH₃)₂ 46.Br H H CH(CH₃)₂ 47. F H H CH(CH₃)₂ 48. CH₃ H H CH(CH₃)₂ 49. C₂H₅ H HCH(CH₃)₂ 50. CH(CH₃)₂ H H CH(CH₃)₂ 51. OCH₃ H H CH(CH₃)₂ 52. CN H HCH(CH₃)₂ 53. CF₃ H H CH(CH₃)₂ 54. OCF₃ H H CH(CH₃)₂ 55. OCHF₂ H HCH(CH₃)₂ 56. Cl H H n-C₄H₉ 57. Br H H n-C₄H₉ 58. F H H n-C₄H₉ 59. CH₃ HH n-C₄H₉ 60. C₂H₅ H H n-C₄H₉ 61. CH(CH₃)₂ H H n-C₄H₉ 62. OCH₃ H H n-C₄H₉63. CN H H n-C₄H₉ 64. CF₃ H H n-C₄H₉ 65. OCF₃ H H n-C₄H₉ 66. OCHF₂ H Hn-C₄H₉ 67. Cl H H C(CH₃)₃ 68. Br H H C(CH₃)₃ 69. F H H C(CH₃)₃ 70. CH₃ HH C(CH₃)₃ 71. C₂H₅ H H C(CH₃)₃ 72. CH(CH₃)₂ H H C(CH₃)₃ 73. OCH₃ H HC(CH₃)₃ 74. CN H H C(CH₃)₃ 75. CF₃ H H C(CH₃)₃ 76. OCF₃ H H C(CH₃)₃ 77.OCHF₂ H H C(CH₃)₃ 78. Cl H H C₆H₅ 79. Br H H C₆H₅ 80. F H H C₆H₅ 81. CH₃H H C₆H₅ 82. C₂H₅ H H C₆H₅ 83. CH(CH₃)₂ H H C₆H₅ 84. OCH₃ H H C₆H₅ 85.CN H H C₆H₅ 86. CF₃ H H C₆H₅ 87. OCF₃ H H C₆H₅ 88. OCHF₂ H H C₆H₅ 89. ClH H cyclopropyl 90. Br H H cyclopropyl 91. F H H cyclopropyl 92. CH₃ H Hcyclopropyl 93. C₂H₅ H H cyclopropyl 94. CH(CH₃)₂ H H cyclopropyl 95.OCH₃ H H cyclopropyl 96. CN H H cyclopropyl 97. CF₃ H H cyclopropyl 98.OCF₃ H H cyclopropyl 99. OCHF₂ H H cyclopropyl 100. Cl H HCH₂-cyclopropyl 101. Br H H CH₂-cyclopropyl 102. F H H CH₂-cyclopropyl103. CH₃ H H CH₂-cyclopropyl 104. C₂H₅ H H CH₂-cyclopropyl 105. CH(CH₃)₂H H CH₂-cyclopropyl 106. OCH₃ H H CH₂-cyclopropyl 107. CN H HCH₂-cyclopropyl 108. CF₃ H H CH₂-cyclopropyl 109. OCF₃ H HCH₂-cyclopropyl 110. OCHF₂ H H CH₂-cyclopropyl 111. Cl H H cyclobutyl112. Br H H cyclobutyl 113. F H H cyclobutyl 114. CH₃ H H cyclobutyl115. C₂H₅ H H cyclobutyl 116. CH(CH₃)₂ H H cyclobutyl 117. OCH₃ H Hcyclobutyl 118. CN H H cyclobutyl 119. CF₃ H H cyclobutyl 120. OCF₃ H Hcyclobutyl 121. OCHF₂ H H cyclobutyl 122. Cl H H cyclopentyl 123. Br H Hcyclopentyl 124. F H H cyclopentyl 125. CH₃ H H cyclopentyl 126. C₂H₅ HH cyclopentyl 127. CH(CH₃)₂ H H cyclopentyl 128. OCH₃ H H cyclopentyl129. CN H H cyclopentyl 130. CF₃ H H cyclopentyl 131. OCF₃ H Hcyclopentyl 132. OCHF₂ H H cyclopentyl 133. Cl H H cyclohexyl 134. Br HH cyclohexyl 135. F H H cyclohexyl 136. CH₃ H H cyclohexyl 137. C₂H₅ H Hcyclohexyl 138. CH(CH₃)₂ H H cyclohexyl 139. OCH₃ H H cyclohexyl 140. CNH H cyclohexyl 141. CF₃ H H cyclohexyl 142. OCF₃ H H cyclohexyl 143.OCHF₂ H H cyclohexyl 144. H Cl H H 145. H Br H H 146. H F H H 147. H CH₃H H 148. H C₂H₅ H H 149. H CH(CH₃)₂ H H 150. H OCH₃ H H 151. H CN H H152. H CF₃ H H 153. H OCF₃ H H 154. H OCHF₂ H H 155. H Cl H CH₃ 156. HBr H CH₃ 157. H F H CH₃ 158. H CH₃ H CH₃ 159. H C₂H₅ H CH₃ 160. HCH(CH₃)₂ H CH₃ 161. H OCH₃ H CH₃ 162. H CN H CH₃ 163. H CF₃ H CH₃ 164. HOCF₃ H CH₃ 165. H OCHF₂ H CH₃ 166. H Cl H C₂H₅ 167. H Br H C₂H₅ 168. H FH C₂H₅ 169. H CH₃ H C₂H₅ 170. H C₂H₅ H C₂H₅ 171. H CH(CH₃)₂ H C₂H₅ 172.H OCH₃ H C₂H₅ 173. H CN H C₂H₅ 174. H CF₃ H C₂H₅ 175. H OCF₃ H C₂H₅ 176.H OCHF₂ H C₂H₅ 177. H Cl H n-C₃H₇ 178. H Br H n-C₃H₇ 179. H F H n-C₃H₇180. H CH₃ H n-C₃H₇ 181. H C₂H₅ H n-C₃H₇ 182. H CH(CH₃)₂ H n-C₃H₇ 183. HOCH₃ H n-C₃H₇ 184. H CN H n-C₃H₇ 185. H CF₃ H n-C₃H₇ 186. H OCF₃ Hn-C₃H₇ 187. H OCHF₂ H n-C₃H₇ 188. H Cl H CH(CH₃)₂ 189. H Br H CH(CH₃)₂190. H F H CH(CH₃)₂ 191. H CH₃ H CH(CH₃)₂ 192. H C₂H₅ H CH(CH₃)₂ 193. HCH(CH₃)₂ H CH(CH₃)₂ 194. H OCH₃ H CH(CH₃)₂ 195. H CN H CH(CH₃)₂ 196. HCF₃ H CH(CH₃)₂ 197. H OCF₃ H CH(CH₃)₂ 198. H OCHF₂ H CH(CH₃)₂ 199. H ClH n-C₄H₉ 200. H Br H n-C₄H₉ 201. H F H n-C₄H₉ 202. H CH₃ H n-C₄H₉ 203. HC₂H₅ H n-C₄H₉ 204. H CH(CH₃)₂ H n-C₄H₉ 205. H OCH₃ H n-C₄H₉ 206. H CN Hn-C₄H₉ 207. H CF₃ H n-C₄H₉ 208. H OCF₃ H n-C₄H₉ 209. H OCHF₂ H n-C₄H₉210. H Cl H C(CH₃)₃ 211. H Br H C(CH₃)₃ 212. H F H C(CH₃)₃ 213. H CH₃ HC(CH₃)₃ 214. H C₂H₅ H C(CH₃)₃ 215. H CH(CH₃)₂ H C(CH₃)₃ 216. H OCH₃ HC(CH₃)₃ 217. H CN H C(CH₃)₃ 218. H CF₃ H C(CH₃)₃ 219. H OCF₃ H C(CH₃)₃220. H OCHF₂ H C(CH₃)₃ 221. H Cl H C₆H₅ 222. H Br H C₆H₅ 223. H F H C₆H₅224. H CH₃ H C₆H₅ 225. H C₂H₅ H C₆H₅ 226. H CH(CH₃)₂ H C₆H₅ 227. H OCH₃H C₆H₅ 228. H CN H C₆H₅ 229. H CF₃ H C₆H₅ 230. H OCF₃ H C₆H₅ 231. HOCHF₂ H C₆H₅ 232. H Cl H cyclopropyl 233. H Br H cyclopropyl 234. H F Hcyclopropyl 235. H CH₃ H cyclopropyl 236. H C₂H₅ H cyclopropyl 237. HCH(CH₃)₂ H cyclopropyl 238. H OCH₃ H cyclopropyl 239. H CN H cyclopropyl240. H CF₃ H cyclopropyl 241. H OCF₃ H cyclopropyl 242. H OCHF₂ Hcyclopropyl 243. H Cl H CH₂-cyclopropyl 244. H Br H CH₂-cyclopropyl 245.H F H CH₂-cyclopropyl 246. H CH₃ H CH₂-cyclopropyl 247. H C₂H₅ HCH₂-cyclopropyl 248. H CH(CH₃)₂ H CH₂-cyclopropyl 249. H OCH₃ HCH₂-cyclopropyl 250. H CN H CH₂-cyclopropyl 251. H CF₃ H CH₂-cyclopropyl252. H OCF₃ H CH₂-cyclopropyl 253. H OCHF₂ H CH₂-cyclopropyl 254. H Cl Hcyclobutyl 255. H Br H cyclobutyl 256. H F H cyclobutyl 257. H CH₃ Hcyclobutyl 258. H C₂H₅ H cyclobutyl 259. H CH(CH₃)₂ H cyclobuty). 260. HOCH₃ H cyclobutyl 261. H CN H cyclobutyl 262. H CF₃ H cyclobutyl 263. HOCF₃ H cyclobutyl 264. H OCHF₂ H cyclobutyl 265. H Cl H cyclopentyl 266.H Br H cyclopentyl 267. H F H cyclopentyl 268. H CH₃ H cyclopentyl 269.H C₂H₅ H cyclopentyl 270. H CH(CH₃)₂ H cyclopentyl 271. H OCH₃ Hcyclopentyl 272. H CN H cyclopentyl 273. H CF₃ H cyclopentyl 274. H OCF₃H cyclopentyl 275. H OCHF₂ H cyclopentyl 276. H Cl H cyclohexyl 277. HBr H cyclohexyl 278. H F H cyclohexyl 279. H CH₃ H cyclohexyl 280. HC₂H₅ H cyclohexyl 281. H CH(CH₃)₂ H cyclohexyl 282. H OCH₃ H cyclohexyl283. H CN H cyclohexyl 284. H CF₃ H cyclohexyl 285. H OCF₃ H cyclohexyl286. H OCHF₂ H cyclohexyl 287. CF₃ Br H H 288. CF₃ OCH₃ H H 289. CF₃ ClH H 290. CF₃ F H H 291. CF₃ CH₃ H H 292. CF₃ C₂H₅ H H 293. CF₃ CF₃ H H294. CF₃ OCF₃ H H 295. CF₃ OCHF₂ H H 296. CF₃ Br H CH₃ 297. CF₃ OCH₃ HCH₃ 298. CF₃ Cl H CH₃ 299. CF₃ F H CH₃ 300. CF₃ CH₃ H CH₃ 301. CF₃ C₂H₅H CH₃ 302. CF₃ CF₃ H CH₃ 303. CF₃ OCF₃ H CH₃ 304. CF₃ OCHF₂ H CH₃ 305.CF₃ Br H C₂H₅ 306. CF₃ OCH₃ H C₂H₅ 307. CF₃ Cl H C₂H₅ 308. CF₃ F H C₂H₅309. CF₃ CH₃ H C₂H₅ 310. CF₃ C₂H₅ H C₂H₅ 311. CF₃ CF₃ H C₂H₅ 312. CF₃OCF₃ H C₂H₅ 313. CF₃ OCHF₂ H C₂H₅ 314. CF₃ Br H n-C₃H₇ 315. CF₃ OCH₃ Hn-C₃H₇ 316. CF₃ Cl H n-C₃H₇ 317. CF₃ F H n-C₃H₇ 318. CF₃ CH₃ H n-C₃H₇319. CF₃ C₂H₅ H n-C₃H₇ 320. CF₃ CF₃ H n-C₃H₇ 321. CF₃ OCF₃ H n-C₃H₇ 322.CF₃ OCHF₂ H n-C₃H₇ 323. CF₃ Br H CH(CH₃)₂ 324. CF₃ OCH₃ H CH(CH₃)₂ 325.CF₃ Cl H CH(CH₃)₂ 326. CF₃ F H CH(CH₃)₂ 327. CF₃ CH₃ H CH(CH₃)₂ 328. CF₃C₂H₅ H CH(CH₃)₂ 329. CF₃ CF₃ H CH(CH₃)₂ 330. CF₃ OCF₃ H CH(CH₃)₂ 331.CF₃ OCHF₂ H CH(CH₃)₂ 332. CF₃ Br H n-C₄H₉ 333. CF₃ OCH₃ H n-C₄H₉ 334.CF₃ Cl H n-C₄H₉ 335. CF₃ F H n-C₄H₉ 336. CF₃ CH₃ H n-C₄H₉ 337. CF₃ C₂H₅H n-C₄H₉ 338. CF₃ CF₃ H n-C₄H₉ 339. CF₃ OCF₃ H n-C₄H₉ 340. CF₃ OCHF₂ Hn-C₄H₉ 341. CF₃ Br H C(CH₃)₃ 342. CF₃ OCH₃ H C(CH₃)₃ 343. CF₃ Cl HC(CH₃)₃ 344. CF₃ F H C(CH₃)₃ 345. CF₃ CH₃ H C(CH₃)₃ 346. CF₃ C₂H₅ HC(CH₃)₃ 347. CF₃ CF₃ H C(CH₃)₃ 348. CF₃ OCF₃ H C(CH₃)₃ 349. CF₃ OCHF₂ HC(CH₃)₃ 350. CF₃ Br H C₆H₅ 351. CF₃ OCH₃ H C₆H₅ 352. CF₃ Cl H C₆H₅ 353.CF₃ F H C₆H₅ 354. CF₃ CH₃ H C₆H₅ 355. CF₃ C₂H₅ H C₆H₅ 356. CF₃ CF₃ HC₆H₅ 357. CF₃ OCF₃ H C₆H₅ 358. CF₃ OCHF₂ H C₆H₅ 359. CF₃ Br Hcyclopropyl 360. CF₃ OCH₃ H cyclopropyl 361. CF₃ Cl H cyclopropyl 362.CF₃ F H cyclopropyl 363. CF₃ CH₃ H cyclopropyl 364. CF₃ C₂H₅ Hcyclopropyl 365. CF₃ CF₃ H cyclopropyl 366. CF₃ OCF₃ H cyclopropyl 367.CF₃ OCHF₂ H cyclopropyl 368. CF₃ Br H CH₂-cyclopropyl 369. CF₃ OCH₃ HCH₂-cyclopropyl 370. CF₃ Cl H CH₂-cyclopropyl 371. CF₃ F HCH₂-cyclopropyl 372. CF₃ CH₃ H CH₂-cyclopropyl 373. CF₃ C₂H₅ HCH₂-cyclopropyl 374. CF₃ CF₃ H CH₂-cyclopropyl 375. CF₃ OCF₃ HCH₂-cyclopropyl 376. CF₃ OCHF₂ H CH₂-cyclopropyl 377. CF₃ Br Hcyclobutyl 378. CF₃ OCH₃ H cyclobutyl 379. CF₃ Cl H cyclobutyl 380. CF₃F H cyclobutyl 381. CF₃ CH₃ H cyclobutyl 382. CF₃ C₂H₅ H cyclobutyl 383.CF₃ CF₃ H cyclobutyl 384. CF₃ OCF₃ H cyclobutyl 385. CF₃ OCHF₂ Hcyclobutyl 386. CF₃ Br H cyclopentyl 387. CF₃ OCH₃ H cyclopentyl 388.CF₃ Cl H cyclopentyl 389. CF₃ F H cyclopentyl 390. CF₃ CH₃ H cyclopentyl391. CF₃ C₂H₅ H cyclopentyl 392. CF₃ CF₃ H cyclopentyl 393. CF₃ OCF₃ Hcyclopentyl 394. CF₃ OCHF₂ H cyclopentyl 395. CF₃ Br H cyclohexyl 396.CF₃ OCH₃ H cyclohexyl 397. CF₃ Cl H cyclohexyl 398. CF₃ F H cyclohexyl399. CF₃ CH₃ H cyclohexyl 400. CF₃ C₂H₅ H cyclohexyl 401. CF₃ CF₃ Hcyclohexyl 402. CF₃ OCF₃ H cyclohexyl 403. CF₃ OCHF₂ H cyclohexyl 404.CF₃ H Br H 405. CF₃ H OCH₃ H 406. CF₃ H Cl H 407. CF₃ H F H 408. CF₃ HCH₃ H 409. CF₃ H C₂H₅ H 410. CF₃ H CF₃ H 411. CF₃ H OCF₃ H 412. CF₃ HOCHF₂ H 413. CF₃ H Br CH₃ 414. CF₃ H OCH₃ CH₃ 415. CF₃ H Cl CH₃ 416. CF₃H F CH₃ 417. CF₃ H CH₃ CH₃ 418. CF₃ H C₂H₅ CH₃ 419. CF₃ H CF₃ CH₃ 420.CF₃ H OCF₃ CH₃ 421. CF₃ H OCHF₂ CH₃ 422. CF₃ H Br C₂H₅ 423. CF₃ H OCH₃C₂H₅ 424. CF₃ H Cl C₂H₅ 425. CF₃ H F C₂H₅ 426. CF₃ H CH₃ C₂H₅ 427. CF₃ HC₂H₅ C₂H₅ 428. CF₃ H CF₃ C₂H₅ 429. CF₃ H OCF₃ C₂H₅ 430. CF₃ H OCHF₂ C₂H₅431. CF₃ H Br n-C₃H₇ 432. CF₃ H OCH₃ n-C₃H₇ 433. CF₃ H Cl n-C₃H₇ 434.CF₃ H F n-C₃H₇ 435. CF₃ H CH₃ n-C₃H₇ 436. CF₃ H C₂H₅ n-C₃H₇ 437. CF₃ HCF₃ n-C₃H₇ 438. CF₃ H OCF₃ n-C₃H₇ 439. CF₃ H OCHF₂ n-C₃H₇ 440. CF₃ H BrCH(CH₃)₂ 441. CF₃ H OCH₃ CH(CH₃)₂ 442. CF₃ H Cl CH(CH₃)₂ 443. CF₃ H FCH(CH₃)₂ 444. CF₃ H CH₃ CH(CH₃)₂ 445. CF₃ H C₂H₅ CH(CH₃)₂ 446. CF₃ H CF₃CH(CH₃)₂ 447. CF₃ H OCF₃ CH(CH₃)₂ 448. CF₃ H OCHF₂ CH(CH₃)₂ 449. CF₃ HBr n-C₄H₉ 450. CF₃ H OCH₃ n-C₄H₉ 451. CF₃ H Cl n-C₄H₉ 452. CF₃ H Fn-C₄H₉ 453. CF₃ H CH₃ n-C₄H₉ 454. CF₃ H C₂H₅ n-C₄H₉ 455. CF₃ H CF₃n-C₄H₉ 456. CF₃ H OCF₃ n-C₄H₉ 457. CF₃ H OCHF₂ n-C₄H₉ 458. CF₃ H BrC(CH₃)₃ 459. CF₃ H OCH₃ C(CH₃)₃ 460. CF₃ H Cl C(CH₃)₃ 461. CF₃ H FC(CH₃)₃ 462. CF₃ H CH₃ C(CH₃)₃ 463. CF₃ H C₂H₅ C(CH₃)₃ 464. CF₃ H CF₃C(CH₃)₃ 465. CF₃ H OCF₃ C(CH₃)₃ 466. CF₃ H OCHF₂ C(CH₃)₃ 467. CF₃ H BrC₆H₅ 468. CF₃ H OCH₃ C₆H₅ 469. CF₃ H Cl C₆H₅ 470. CF₃ H F C₆H₅ 471. CF₃H CH₃ C₆H₅ 472. CF₃ H C₂H₅ C₆H₅ 473. CF₃ H CF₃ C₆H₅ 474. CF₃ H OCF₃ C₆H₅475. CF₃ H OCHF₂ C₆H₅ 476. CF₃ H Br cyclopropyl 477. CF₃ H OCH₃cyclopropyl 478. CF₃ H Cl cyclopropyl 479. CF₃ H F cyclopropyl 480. CF₃H CH₃ cyclopropyl 481. CF₃ H C₂H₅ cyclopropyl 482. CF₃ H CF₃ cyclopropyl483. CF₃ H OCF₃ cyclopropyl 484. CF₃ H OCHF₂ cyclopropyl 485. CF₃ H BrCH₂-cyclopropyl 486. CF₃ H OCH₃ CH₂-cyclopropyl 487. CF₃ H ClCH₂-cyclopropyl 488. CF₃ H F CH₂-cyclopropyl 489. CF₃ H CH₃CH₂-cyclopropyl 490. CF₃ H C₂H₅ CH₂-cyclopropyl 491. CF₃ H CF₃CH₂-cyclopropyl 492. CF₃ H OCF₃ CH₂-cyclopropyl 493. CF₃ H OCHF₂CH₂-cyclopropyl 494. CF₃ H Br cyclobutyl 495. CF₃ H OCH₃ cyclobutyl 496.CF₃ H Cl cyclobutyl 497. CF₃ H F cyclobutyl 498. CF₃ H CH₃ cyclobutyl499. CF₃ H C₂H₅ cyclobutyl 500. CF₃ H CF₃ cyclobutyl 501. CF₃ H OCF₃cyclobutyl 502. CF₃ H OCHF₂ cyclobutyl 503. CF₃ H Br cyclopentyl 504.CF₃ H OCH₃ cyclopentyl 505. CF₃ H Cl cyclopentyl 506. CF₃ H Fcyclopentyl 507. CF₃ H CH₃ cyclopentyl 508. CF₃ H C₂H₅ cyclopentyl 509.CF₃ H CF₃ cyclopentyl 510. CF₃ H OCF₃ cyclopentyl 511. CF₃ H OCHF₂cyclopentyl 512. CF₃ H Br cyclohexyl 513. CF₃ H OCH₃ cyclohexyl 514. CF₃H Cl cyclohexyl 515. CF₃ H F cyclohexyl 516. CF₃ H CH₃ cyclohexyl 517.CF₃ H C₂H₅ cyclohexyl 518. CF₃ H CF₃ cyclohexyl 519. CF₃ H OCF₃cyclohexyl 520. CF₃ H OCHF₂ cyclohexyl 521. OCF₃ Br H H 522. OCF₃ OCH₃ HH 523. OCF₃ Cl H H 524. OCF₃ F H H 525. OCF₃ CH₃ H H 526. OCF₃ C₂H₅ H H527. OCF₃ CF₃ H H 528. OCF₃ OCF₃ H H 529. OCF₃ OCHF₂ H H 530. OCF₃ Br HCH₃ 531. OCF₃ OCH₃ H CH₃ 532. OCF₃ Cl H CH₃ 533. OCF₃ F H CH₃ 534. OCF₃Cl3 H CH₃ 535. OCF₃ C₂H₅ H CH₃ 536. OCF₃ CF₃ H CH₃ 537. OCF₃ OCF₃ H CH₃538. OCF₃ OCHF₂ H CH₃ 539. OCF₃ Br H C₂H₅ 540. OCF₃ OCH₃ H C₂H₅ 541.OCF₃ Cl H C₂H₅ 542. OCF₃ F H C₂H₅ 543. OCF₃ CH₃ H C₂H₅ 544. OCF₃ C₂H₅ HC₂H₅ 545. OCF₃ CF₃ H C₂H₅ 546. OCF₃ OCF₃ H C₂H₅ 547. OCF₃ OCHF₂ H C₂H₅548. OCF₃ Br H n-C₃H₇ 549. OCF₃ OCH₃ H n-C₃H₇ 550. OCF₃ Cl H n-C₃H₇ 551.OCF₃ F H n-C₃H₇ 552. OCF₃ CH₃ H n-C₃H₇ 553. OCF₃ C₂H₅ H n-C₃H₇ 554. OCF₃CF₃ H n-C₃H₇ 555. OCF₃ OCF₃ H n-C₃H₇ 556. OCF₃ OCHF₂ H n-C₃H₇ 557. OCF₃Br H CH(CH₃)₂ 558. OCF₃ OCH₃ H CH(CH₃)₂ 559. OCF₃ Cl H CH(CH₃)₂ 560.OCF₃ F H CH(CH₃)₂ 561. OCF₃ CH₃ H CH(CH₃)₂ 562. OCF₃ C₂H₅ H CH(CH₃)₂563. OCF₃ CF₃ H CH(CH₃)₂ 564. OCF₃ OCF₃ H CH(CH₃)₂ 565. OCF₃ OCHF₂ HCH(CH₃)₂ 566. OCF₃ Br H n-C₄H₉ 567. OCF₃ OCH₃ H n-C₄H₉ 568. OCF₃ Cl Hn-C₄H₉ 569. OCF₃ F H n-C₄H₉ 570. OCF₃ CH₃ H n-C₄H₉ 571. OCF₃ C₂H₅ Hn-C₄H₉ 572. OCF₃ CF₃ H n-C₄H₉ 573. OCF₃ OCF₃ H n-C₄H₉ 574. OCF₃ OCHF₂ Hn-C₄H₉ 575. OCF₃ Br H C(CH₃)₃ 576. OCF₃ OCH₃ H C(CH₃)₃ 577. OCF₃ Cl HC(CH₃)₃ 578. OCF₃ F H C(CH₃)₃ 579. OCF₃ CH₃ H C(CH₃)₃ 580. OCF₃ C₂H₅ HC(CH₃)₃ 581. OCF₃ CF₃ H C(CH₃)₃ 582. OCF₃ OCF₃ H C(CH₃)₃ 583. OCF₃ OCHF₂H C(CH₃)₃ 584. OCF₃ Br H C₆H₅ 585. OCF₃ OCH₃ H C₆H₅ 586. OCF₃ Cl H C₆H₅587. OCF₃ F H C₆H₅ 588. OCF₃ CH₃ H C₆H₅ 589. OCF₃ C₂H₅ H C₆H₅ 590. OCF₃CF₃ H C₆H₅ 591. OCF₃ OCF₃ H C₆H₅ 592. OCF₃ OCHF₂ H C₆H₅ 593. OCF₃ Br Hcyclopropyl 594. OCF₃ OCH₃ H cyclopropyl 595. OCF₃ Cl H cyclopropyl 596.OCF₃ F H cyclopropyl 597. OCF₃ CH₃ H cyclopropyl 598. OCF₃ C₂H₅ Hcyclopropyl 599. OCF₃ CF₃ H cyclopropyl 600. OCF₃ OCF₃ H cyclopropyl601. OCF₃ OCHF₂ H cyclopropyl 602. OCF₃ Br H CH₂-cyclopropyl 603. OCF₃OCH₃ H CH₂-cyclopropyl 604. OCF₃ Cl H CH₂-cyclopropyl 605. OCF₃ F HCH₂-cyclopropyl 606. OCF₃ CH₃ H CH₂-cyclopropyl 607. OCF₃ C₂H₅ HCH₂-cyclopropyl 608. OCF₃ OCF₃ H CH₂-cyclopropyl 609. OCF₃ CF₃ HCH₂-cyclopropyl 610. OCF₃ OCHF₂ H CH₂-cyclopropyl 611. OCF₃ Br Hcyclobutyl 612. OCF₃ OCH₃ H cyclobutyl 613. OCF₃ Cl H cyclobutyl 614.OCF₃ F H cyclobutyl 615. OCF₃ CH₃ H cyclobutyl 616. OCF₃ C₂H₅ Hcyclobutyl 617. OCF₃ QCF₃ H cyclobutyl 618. OCF₃ CF₃ H cyclobutyl 619.OCF₃ OCHF₂ H cyclobutyl 620. OCF₃ Br H cyclopentyl 621. OCF₃ OCH₃ Hcyclopentyl 622. OCF₃ Cl H cyclopentyl 623. OCF₃ F H cyclopentyl 624.OCF₃ CH₃ H cyclopentyl 625. OCF₃ C₂H₅ H cyclopentyl 626. OCF₃ OCF₃ Hcyclopentyl 627. OCF₃ CF₃ H cyclopentyl 628. OCF₃ OCHF₂ H cyclopentyl629. OCF₃ Br H cyclohexyl 630. OCF₃ OCH₃ H cyclohexyl 631. OCF₃ Cl Hcyclohexyl 632. OCF₃ F H cyclohexyl 633. OCF₃ CH₃ H cyclohexyl 634. OCF₃C₂H₅ H cyclohexyl 635. OCF₃ OCF₃ H cyclohexyl 636. OCF₃ CF₃ H cyclohexyl637. OCF₃ OCHF₂ H cyclohexyl 638. OCF₃ H Br H 639. OCF₃ H OCH₃ H 640.OCF₃ H Cl H 641. OCF₃ H F H 642. OCF₃ H CH₃ H 643. OCF₃ H C₂H₅ H 644.OCF₃ H CF₃ H 645. OCF₃ H OCF₃ H 646. OCF₃ H OCHF₂ H 647. OCF₃ H Br CH₃648. OCF₃ H OCH₃ CH₃ 649. OCF₃ H Cl CH₃ 650. OCF₃ H F CH₃ 651. OCF₃ HCH₃ CH₃ 652. OCF₃ H C₂H₅ CH₃ 653. OCF₃ H CF₃ CH₃ 654. OCF₃ H OCF₃ CH₃655. OCF₃ H OCHF₂ CH₃ 656. OCF₃ H Br C₂H₅ 657. OCF₃ H OCH₃ C₂H₅ 658.OCF₃ H Cl C₂H₅ 659. OCF₃ H F C₂H₅ 660. OCF₃ H CH₃ C₂H₅ 661. OCF₃ H C₂H₅C₂H₅ 662. OCF₃ H CF₃ C₂H₅ 663. OCF₃ H OCF₃ C₂H₅ 664. OCF₃ H OCHF₂ C₂H₅665. OCF₃ H Br n-C₃H₇ 666. OCF₃ H OCH₃ n-C₃H₇ 667. OCF₃ H Cl n-C₃H₇ 668.OCF₃ H F n-C₃H₇ 669. OCF₃ H CH₃ n-C₃H₇ 670. OCF₃ H C₂H₅ n-C₃H₇ 671. OCF₃H CF₃ n-C₃H₇ 672. OCF₃ H OCF₃ n-C₃H₇ 673. OCF₃ H OCHF₂ n-C₃H₇ 674. OCF₃H Br CH(CH₃)₂ 675. OCF₃ H OCH₃ CH(CH₃)₂ 676. OCF₃ H Cl CH(CH₃)₂ 677.OCF₃ H F CH(CH₃)₂ 678. OCF₃ H CH₃ CH(CH₃)₂ 679. OCF₃ H C₂H₅ CH(CH₃)₂680. OCF₃ H CF₃ CH(CH₃)₂ 681. OCF₃ H OCF₃ CH(CH₃)₂ 682. OCF₃ H OCHF₂CH(CH₃)₂ 683. OCF₃ H Br n-C₄H₉ 684. OCF₃ H OCH₃ n-C₄H₉ 685. OCF₃ H Cln-C₄H₉ 686. OCF₃ H F n-C₄H₉ 687. OCF₃ H CH₃ n-C₄H₉ 688. OCF₃ H C₂H₅n-C₄H₉ 689. OCF₃ H CF₃ n-C₄H₉ 690. OCF₃ H OCF₃ n-C₄H₉ 691. OCF₃ H OCHF₂n-C₄H₉ 692. OCF₃ H Br C(CH₃)₃ 693. OCF₃ H OCH₃ C(CH₃)₃ 694. OCF₃ H ClC(CH₃)₃ 695. OCF₃ H F C(CH₃)₃ 696. OCF₃ H CH₃ C(CH₃)₃ 697. OCF₃ H C₂H₅C(CH₃)₃ 698. OCF₃ H CF₃ C(CH₃)₃ 699. OCF₃ H OCF₃ C(CH₃)₃ 700. OCF₃ HOCHF₂ C(CH₃)₃ 701. OCF₃ H Br C₆H₅ 702. OCF₃ H OCH₃ C₆H₅ 703. OCF₃ H ClC₆H₅ 704. OCF₃ H F C₆H₅ 705. OCF₃ H CH₃ C₆H₅ 706. OCF₃ H C₂H₅ C₆H₅ 707.OCF₃ H CF₃ C₆H₅ 708. OCF₃ H OCF₃ C₆H₅ 709. OCF₃ H OCHF₂ C₆H₅ 710. OCF₃ HBr cyclopropyl 711. OCF₃ H OCH₃ cyclopropyl 712. OCF₃ H Cl cyclopropyl713. OCF₃ H F cyclopropyl 714. OCF₃ H CH₃ cyclopropyl 715. OCF₃ H C₂H₅cyclopropyl 716. OCF₃ H CF₃ cyclopropyl 717. OCF₃ H OCF₃ cyclopropyl718. OCF₃ H OCHF₂ cyclopropyl 719. OCF₃ H Br CH₂-cyclopropyl 720. OCF₃ HOCH₃ CH₂-cyclopropyl 721. OCF₃ H Cl CH₂-cyclopropyl 722. OCF₃ H FCH₂-cyclopropyl 723. OCF₃ H CH₃ CH₂-cyclopropyl 724. OCF₃ H C₂H₅CH₂-cyclopropyl 725. OCF₃ H CF₃ CH₂-cyclopropyl 726. OCF₃ H OCF₃CH₂-cyclopropyl 727. OCF₃ H OCHF₂ CH₂-cyclopropyl 728. OCF₃ H Brcyclobutyl 729. OCF₃ H OCH₃ cyclobutyl 730. OCF₃ H Cl cyclobutyl 731.OCF₃ H F cyclobutyl 732. OCF₃ H CH₃ cyclobutyl 733. OCF₃ H C₂H₅cyclobutyl 734. OCF₃ H CF₃ cyclobutyl 735. OCF₃ H OCF₃ cyclobutyl 736.OCF₃ H OCHF₂ cyclobutyl 737. OCF₃ H Br cyclopentyl 738. OCF₃ H OCH₃cyclopentyl 739. OCF₃ H Cl cyclopentyl 740. OCF₃ H F cyclopentyl 741.OCF₃ H CH₃ cyclopentyl 742. OCF₃ H C₂H₅ cyclopentyl 743. OCF₃ H CF₃cyclopentyl 744. OCF₃ H OCF₃ cyclopentyl 745. OCF₃ H OCHF₂ cyclopentyl746. OCF₃ H Br cyclohexyl 747. OCF₃ H OCH₃ cyclohexyl 748. OCF₃ H Clcyclohexyl 749. OCF₃ H F cyclohexyl 750. OCF₃ H CH₃ cyclohexyl 751. OCF₃H C₂H₅ cyclohexyl 752. OCF₃ H CF₃ cyclohexyl 753. OCF₃ H OCF₃ cyclohexyl754. OCF₃ H OCHF₂ cyclohexyl 755. OCHF₂ Br H H 756. OCHF₂ OCH₃ H H 757.OCHF₂ Cl H H 758. OCHF₂ F H H 759. OCHF₂ CH₃ H H 760. OCHF₂ C₂H₅ H H761. OCHF₂ OCF₃ H H 762. OCHF₂ CF₃ H H 763. OCHF₂ Br H CH₃ 764. OCHF₂OCH₃ H CH₃ 765. OCHF₂ Cl H CH₃ 766. OCHF₂ F H CH₃ 767. OCHF₂ CH₃ H CH₃768. OCHF₂ C₂H₅ H CH₃ 769. OCHF₂ OCF₃ H CH₃ 770. OCHF₂ CF₃ H CH₃ 771.OCHF₂ Br H C₂H₅ 772. OCHF₂ OCH₃ H C₂H₅ 773. OCHF₂ Cl H C₂H₅ 774. OCHF₂ FH C₂H₅ 775. OCHF₂ CH₃ H C₂H₅ 776. OCHF₂ C₂H₅ H C₂H₅ 777. OCHF₂ OCF₃ HC₂H₅ 778. OCHF₂ CF₃ H C₂H₅ 779. OCHF₂ Br H n-C₃H₇ 780. OCHF₂ OCH₃ Hn-C₃H₇ 781. OCHF₂ Cl H n-C₃H₇ 782. OCHF₂ F H n-C₃H₇ 783. OCHF₂ CH₃ Hn-C₃H₇ 784. OCHF₂ C₂H₅ H n-C₃H₇ 785. OCHF₂ OCF₃ H n-C₃H₇ 786. OCHF₂ CF₃H n-C₃H₇ 787. OCHF₂ Br H CH(CH₃)₂ 788. OCHF₂ OCH₃ H CH(CH₃)₂ 789. OCHF₂Cl H CH(CH₃)₂ 790. OCHF₂ F H CH(CH₃)₂ 791. OCHF₂ CH₃ H CH(CH₃)₂ 792.OCHF₂ C₂H₅ H CH(CH₃)₂ 793. OCHF₂ OCF₃ H CH(CH₃)₂ 794. OCHF₂ CF₃ HCH(CH₃)₂ 795. OCHF₂ Br H n-C₄H₉ 796. OCHF₂ OCH₃ H n-C₄H₉ 797. OCHF₂ Cl Hn-C₄H₉ 798. OCHF₂ F H n-C₄H₉ 799. OCHF₂ CH₃ H n-C₄H₉ 800. OCHF₂ C₂H₅ Hn-C₄H₉ 801. OCHF₂ OCF₃ H n-C₄H₉ 802. OCHF₂ CF₃ H n-C₄H₉ 803. OCHF₂ Br HC(CH₃)₃ 804. OCHF₂ OCH₃ H C(CH₃)₃ 805. OCHF₂ Cl H C(CH₃)₃ 806. OCHF₂ F HC(CH₃)₃ 807. OCHF₂ CH₃ H C(CH₃)₃ 808. OCHF₂ C₂H₅ H C(CH₃)₃ 809. OCHF₂OCF₃ H C(CH₃)₃ 810. OCHF₂ CF₃ H C(CH₃)₃ 811. OCHF₂ Br H C₆H₅ 812. OCHF₂OCH₃ H C₆H₅ 813. OCHF₂ Cl H C₆H₅ 814. OCHF₂ F H C₆H₅ 815. OCHF₂ CH₃ HC₆H₅ 816. OCHF₂ C₂H₅ H C₆H₅ 817. OCHF₂ OCF₃ H C₆H₅ 818. OCHF₂ CF₃ H C₆H₅819. OCHF₂ Br H cyclopropyl 820. OCHF₂ OCH₃ H cyclopropyl 821. OCHF₂ ClH cyclopropyl 822. OCHF₂ F H cyclopropyl 823. OCHF₂ CH₃ H cyclopropyl824. OCHF₂ C₂H₅ H cyclopropyl 825. OCHF₂ OCF₃ H cyclopropyl 826. OCHF₂CF₃ H cyclopropyl 827. OCHF₂ Br H CH₂-cyclopropyl 828. OCHF₂ OCH₃ HCH₂-cyclopropyl 829. OCHF₂ Cl H CH₂-cyclopropyl 830. OCHF₂ F HCH₂-cyclopropyl 831. OCHF₂ CH₃ H CH₂-cyclopropyl 832. OCHF₂ C₂H₅ HCH₂-cyclopropyl 833. OCHF₂ OCF₃ H CH₂-cyclopropyl 834. OCHF₂ CF₃ HCH₂-cyclopropyl 835. OCHF₂ Br H cyclobutyl 836. OCHF₂ OCH₃ H cyclobutyl837. OCHF₂ Cl H cyclobutyl 838. OCHF₂ F H cyclobutyl 839. OCHF₂ CH₃ Hcyclobutyl 840. OCHF₂ C₂H₅ H cyclobutyl 841. OCHF₂ OCF₃ H cyclobutyl842. OCHF₂ CF₃ H cyclobutyl 843. OCHF₂ Br H cyclopentyl 844. OCHF₂ OCH₃H cyclopentyl 845. OCHF₂ Cl H cyclopentyl 846. OCHF₂ F H cyclopentyl847. OCHF₂ CH₃ H cyclopentyl 848. OCHF₂ C₂H₅ H cyclopentyl 849. OCHF₂OCF₃ H cyclopentyl 850. OCHF₂ CF₃ H cyclopentyl 851. OCHF₂ Br Hcyclohexyl 852. OCHF₂ OCH₃ H cyclohexyl 853. OCHF₂ Cl H cyclohexyl 854.OCHF₂ F H cyclohexyl 855. OCHF₂ CH₃ H cyclohexyl 856. OCHF₂ C₂H₅ Hcyclohexyl 857. OCHF₂ OCF₃ H cyclohexyl 858. OCHF₂ CF₃ H cyclohexyl 859.OCHF₂ H Br H 860. OCHF₂ H OCH₃ H 861. OCHF₂ H Cl H 862. OCHF₂ H F H 863.OCHF₂ H CH₃ H 864. OCHF₂ H C₂H₅ H 865. OCHF₂ H OCF₃ H 866. OCHF₂ H CF₃ H867. OCHF₂ H Br CH₃ 868. OCHF₂ H OCH₃ CH₃ 869. OCHF₂ H Cl CH₃ 870. OCHF₂H F CH₃ 871. OCHF₂ H CH₃ CH₃ 872. OCHF₂ H C₂H₅ CH₃ 873. OCHF₂ H OCF₃ CH₃874. OCHF₂ H CF₃ CH₃ 875. OCHF₂ H Br C₂H₅ 876. OCHF₂ H OCH₃ C₂H₅ 877.OCHF₂ H Cl C₂H₅ 878. OCHF₂ H F C₂H₅ 879. OCHF₂ H CH₃ C₂H₅ 880. OCHF₂ HC₂H₅ C₂H₅ 881. OCHF₂ H OCF₃ C₂H₅ 882. OCHF₂ H CF₃ C₂H₅ 883. OCHF₂ H Brn-C₃H₇ 884. OCHF₂ H OCH₃ n-C₃H₇ 885. OCHF₂ H Cl n-C₃H₇ 886. OCHF₂ H Fn-C₃H₇ 887. OCHF₂ H CH₃ n-C₃H₇ 888. OCHF₂ H C₂H₅ n-C₃H₇ 889. OCHF₂ HOCF₃ n-C₃H₇ 890. OCHF₂ H CF₃ n-C₃H₇ 891. OCHF₂ H Br CH(CH₃)₂ 892. OCHF₂H OCH₃ CH(CH₃)₂ 893. OCHF₂ H Cl CH(CH₃)₂ 894. OCHF₂ H F CH(CH₃)₂ 895.OCHF₂ H CH₃ CH(CH₃)₂ 896. OCHF₂ H C₂H₅ CH(CH₃)₂ 897. OCHF₂ H OCF₃CH(CH₃)₂ 898. OCHF₂ H CF₃ CH(CH₃)₂ 899. OCHF₂ H Br n-C₄H₉ 900. OCHF₂ HOCH₃ n-C₄H₉ 901. OCHF₂ H Cl n-C₄H₉ 902. OCHF₂ H F n-C₄H₉ 903. OCHF₂ HCH₃ n-C₄H₉ 904. OCHF₂ H C₂H₅ n-C₄H₉ 905. OCHF₂ H OCF₃ n-C₄H₉ 906. OCHF₂H CF₃ n-C₄H₉ 907. OCHF₂ H Br C(CH₃)₃ 908. OCHF₂ H OCH₃ C(CH₃)₃ 909.OCHF₂ H Cl C(CH₃)₃ 910. OCHF₂ H F C(CH₃)₃ 911. OCHF₂ H CH₃ C(CH₃)₃ 912.OCHF₂ H C₂H₅ C(CH₃)₃ 913. OCHF₂ H OCF₃ C(CH₃)₃ 914. OCHF₂ H CF₃ C(CH₃)₃915. OCHF₂ H Br C₆H₅ 916. OCHF₂ H OCH₃ C₆H₅ 917. OCHF₂ H Cl C₆H₅ 918.OCHF₂ H F C₆H₅ 919. OCHF₂ H CH₃ C₆H₅ 920. OCHF₂ H C₂H₅ C₆H₅ 921. OCHF₂ HOCF₃ C₆H₅ 922. OCHF₂ H CF₃ C₆H₅ 923. OCHF₂ H Br cyclopropyl 924. OCHF₂ HOCH₃ cyclopropyl 925. OCHF₂ H Cl cyclopropyl 926. OCHF₂ H F cyclopropyl927. OCHF₂ H CH₃ cyclopropyl 928. OCHF₂ H C₂H₅ cyclopropyl 929. OCHF₂ HOCF₃ cyclopropyl 930. OCHF₂ H CF₃ cyclopropyl 931. OCHF₂ H BrCH₂-cyclopropyl 932. OCHF₂ H OCH₃ CH₂-cyclopropyl 933. OCHF₂ H ClCH₂-cyclopropyl 934. OCHF₂ H F CH₂-cyclopropyl 935. OCHF₂ H CH₃CH₂-cyclopropyl 936. OCHF₂ H C₂H₅ CH₂-cyclopropyl 937. OCHF₂ H OCF₃CH₂-cyclopropyl 938. OCHF₂ H CF₃ CH₂-cyclopropyl 939. OCHF₂ H Brcyclobutyl 940. OCHF₂ H OCH₃ cyclobutyl 941. OCHF₂ H Cl cyclobutyl 942.OCHF₂ H F cyclobutyl 943. OCHF₂ H CH₃ cyclobutyl 944. OCHF₂ H C₂H₅cyclobutyl 945. OCHF₂ H OCF₃ cyclobutyl 946. OCHF₂ H CF₃ cyclobutyl 947.OCHF₂ H Br cyclopentyl 948. OCHF₂ H OCH₃ cyclopentyl 949. OCHF₂ H Clcyclopentyl 950. OCHF₂ H F cyclopentyl 951. OCHF₂ H CH₃ cyclopentyl 952.OCHF₂ H C₂H₅ cyclopentyl 953. OCHF₂ H OCF₃ cyclopentyl 954. OCHF₂ H CF₃cyclopentyl 955. OCHF₂ H Br cyclohexyl 956. OCHF₂ H OCH₃ cyclohexyl 957.OCHF₂ H Cl cyclohexyl 958. OCHF₂ H F cyclohexyl 959. OCHF₂ H CH₃cyclohexyl 960. OCHF₂ H C₂H₅ cyclohexyl 961. OCHF₂ H OCF₃ cyclohexyl962. OCHF₂ H CF₃ cyclohexyl 963. OCH₃ Br H H 964. OCH₃ OCH₃ H H 965.OCH₃ Cl H H 966. OCH₃ F H H 967. OCH₃ CH₃ H H 968. OCH₃ C₂H₅ H H 969.OCH₃ CF₃ H H 970. OCH₃ OCF₃ H H 971. OCH₃ OCHF₂ H H 972. OCH₃ Br H CH₃973. OCH₃ OCH₃ H CH₃ 974. OCH₃ Cl H CH₃ 975. OCH₃ F H CH₃ 976. OCH₃ CH₃H CH₃ 977. OCH₃ C₂H₅ H CH₃ 978. OCH₃ CF₃ H CH₃ 979. OCH₃ OCF₃ H CH₃ 980.OCH₃ OCHF₂ H CH₃ 981. OCH₃ Br H C₂H₅ 982. OCH₃ OCH₃ H C₂H₅ 983. OCH₃ ClH C₂H₅ 984. OCH₃ F H C₂H₅ 985. OCH₃ CH₃ H C₂H₅ 986. OCH₃ C₂H₅ H C₂H₅987. OCH₃ CF₃ H C₂H₅ 988. OCH₃ OCF₃ H C₂H₅ 989. OCH₃ OCHF₂ H C₂H₅ 990.OCH₃ Br H n-C₃H₇ 991. OCH₃ OCH₃ H n-C₃H₇ 992. OCH₃ Cl H n-C₃H₇ 993. OCH₃F H n-C₃H₇ 994. OCH₃ CH₃ H n-C₃H₇ 995. OCH₃ C₂H₅ H n-C₃H₇ 996. OCH₃ CF₃H n-C₃H₇ 997. OCH₃ OCF₃ H n-C₃H₇ 998. OCH₃ OCHF₂ H n-C₃H₇ 999. OCH₃ Br HCH(CH₃)₂ 1000. OCH₃ OCH₃ H CH(CH₃)₂ 1001. OCH₃ Cl H CH(CH₃)₂ 1002. OCH₃F H CH(CH₃)₂ 1003. OCH₃ CH₃ H CH(CH₃)₂ 1004. OCH₃ C₂H₅ H CH(CH₃)₂ 1005.OCH₃ CF₃ H CH(CH₃)₂ 1006. OCH₃ OCF₃ H CH(CH₃)₂ 1007. OCH₃ OCHF₂ HCH(CH₃)₂ 1008. OCH₃ Br H n-C₄H₉ 1009. OCH₃ OCH₃ H n-C₄H₉ 1010. OCH₃ Cl Hn-C₄H₉ 1011. OCH₃ F H n-C₄H₉ 1012. OCH₃ CH₃ H n-C₄H₉ 1013. OCH₃ C₂H₅ Hn-C₄H₉ 1014. OCH₃ CF₃ H n-C₄H₉ 1015. OCH₃ OCF₃ H n-C₄H₉ 1016. OCH₃ OCHF₂H n-C₄H₉ 1017. OCH₃ Br H C(CH₃)₃ 1018. OCH₃ OCH₃ H C(CH₃)₃ 1019. OCH₃ ClH C(CH₃)₃ 1020. OCH₃ F H C(CH₃)₃ 1021. OCH₃ CH₃ H C(CH₃)₃ 1022. OCH₃C₂H₅ H C(CH₃)₃ 1023. OCH₃ CF₃ H C(CH₃)₃ 1024. OCH₃ OCF₃ H C(CH₃)₃ 1025.OCH₃ OCHF₂ H C(CH₃)₃ 1026. OCH₃ Br H C₆H₅ 1027. OCH₃ OCH₃ H C₆H₅ 1028.OCH₃ Cl H C₆H₅ 1029. OCH₃ F H C₆H₅ 1030. OCH₃ CH₃ H C₆H₅ 1031. OCH₃ C₂H₅H C₆H₅ 1032. OCH₃ CF₃ H C₆H₅ 1033. OCH₃ OCF₃ H C₆H₅ 1034. OCH₃ OCHF₂ HC₆H₅ 1035. OCH₃ Br H cyclopropyl 1036. OCH₃ OCH₃ H cyclopropyl 1037.OCH₃ Cl H cyclopropyl 1038. OCH₃ F H cyclopropyl 1039. OCH₃ CH₃ Hcyclopropyl 1040. OCH₃ C₂H₅ H cyclopropyl 1041. OCH₃ CF₃ H cyclopropyl1042. OCH₃ OCF₃ H cyclopropyl 1043. OCH₃ OCHF₂ H cyclopropyl 1044. OCH₃Br H CH₂-cyclopropyl 1045. OCH₃ OCH₃ H CH₂-cyclopropyl 1046. OCH₃ Cl HCH₂-cyclopropyl 1047. OCH₃ F H CH₂-cyclopropyl 1048. OCH₃ CH₃ HCH₂-cyclopropyl 1049. OCH₃ C₂H₅ H CH₂-cyclopropyl 1050. OCH₃ CF₃ HCH₂-cyclopropyl 1051. OCH₃ OCF₃ H CH₂-cyclopropyl 1052. OCH₃ OCHF₂ HCH₂-cyclopropyl 1053. OCH₃ Br H cyclobutyl 1054. OCH₃ OCH₃ H cyclobutyl1055. OCH₃ Cl H cyclobutyl 1056. OCH₃ F H cyclobutyl 1057. OCH₃ CH₃ Hcyclobutyl 1058. OCH₃ C₂H₅ H cyclobutyl 1059. OCH₃ CF₃ H cyclobutyl1060. OCH₃ OCF₃ H cyclobutyl 1061. OCH₃ OCHF₂ H cyclobutyl 1062. OCH₃ BrH cyclopentyl 1063. OCH₃ OCH₃ H cyclopentyl 1064. OCH₃ Cl H cyclopentyl1065. OCH₃ F H cyclopentyl 1066. OCH₃ CH₃ H cyclopentyl 1067. OCH₃ C₂H₅H cyclopentyl 1068. OCH₃ CF₃ H cyclopentyl 1069. OCH₃ OCF₃ H cyclopentyl1070. OCH₃ OCHF₂ H cyclopentyl 1071. OCH₃ Br H cyclohexyl 1072. OCH₃OCH₃ H cyclohexyl 1073. OCH₃ Cl H cyclohexyl 1074. OCH₃ F H cyclohexyl1075. OCH₃ CH₃ H cyclohexyl 1076. OCH₃ C₂H₅ H cyclohexyl 1077. OCH₃ CF₃H cyclohexyl 1078. OCH₃ OCF₃ H cyclohexyl 1079. OCH₃ OCHF₂ H cyclohexyl1080. OCH₃ H Br H 1081. OCH₃ H OCH₃ H 1082. OCH₃ H Cl H 1083. OCH₃ H F H1084. OCH₃ H CH₃ H 1085. OCH₃ H C₂H₅ H 1086. OCH₃ H CF₃ H 1087. OCH₃ HOCF₃ H 1088. OCH₃ H OCHF₂ H 1089. OCH₃ H Br CH₃ 1090. OCH₃ H OCH₃ CH₃1091. OCH₃ H Cl CH₃ 1092. OCH₃ H F CH₃ 1093. OCH₃ H CH₃ CH₃ 1094. OCH₃ HC₂H₅ CH₃ 1095. OCH₃ H CF₃ CH₃ 1096. OCH₃ H OCF₃ CH₃ 1097. OCH₃ H OCHF₂CH₃ 1098. OCH₃ H Br C₂H₅ 1099. OCH₃ H OCH₃ C₂H₅ 1100. OCH₃ H Cl C₂H₅1101. OCH₃ H F C₂H₅ 1102. OCH₃ H CH₃ C₂H₅ 1103. OCH₃ H C₂H₅ C₂H₅ 1104.OCH₃ H CF₃ C₂H₅ 1105. OCH₃ H OCF₃ C₂H₅ 1106. OCH₃ H OCHF₂ C₂H₅ 1107.OCH₃ H Br n-C₃H₇ 1108. OCH₃ H OCH₃ n-C₃H₇ 1109. OCH₃ H Cl n-C₃H₇ 1110.OCH₃ H F n-C₃H₇ 1111. OCH₃ H CH₃ n-C₃H₇ 1112. OCH₃ H C₂H₅ n-C₃H₇ 1113.OCH₃ H CF₃ n-C₃H₇ 1114. OCH₃ H OCF₃ n-C₃H₇ 1115. OCH₃ H OCHF₂ n-C₃H₇1116. OCH₃ H Br CH(CH₃)₂ 1117. OCH₃ H OCH₃ CH(CH₃)₂ 1118. OCH₃ H ClCH(CH₃)₂ 1119. OCH₃ H F CH(CH₃)₂ 1120. OCH₃ H CH₃ CH(CH₃)₂ 1121. OCH₃ HC₂H₅ CH(CH₃)₂ 1122. OCH₃ H CF₃ CH(CH₃)₂ 1123. OCH₃ H OCF₃ CH(CH₃)₂ 1124.OCH₃ H OCHF₂ CH(CH₃)₂ 1125. OCH₃ H Br n-C₄H₉ 1126. OCH₃ H OCH₃ n-C₄H₉1127. OCH₃ H Cl n-C₄H₉ 1128. OCH₃ H F n-C₄H₉ 1129. OCH₃ H CH₃ n-C₄H₉1130. OCH₃ H C₂H₅ n-C₄H₉ 1131. OCH₃ H CF₃ n-C₄H₉ 1132. OCH₃ H OCF₃n-C₄H₉ 1133. OCH₃ H OCHF₂ n-C₄H₉ 1134. OCH₃ H Br C(CH₃)₃ 1135. OCH₃ HOCH₃ C(CH₃)₃ 1136. OCH₃ H Cl C(CH₃)₃ 1137. OCH₃ H F C(CH₃)₃ 1138. OCH₃ HCH₃ C(CH₃)₃ 1139. OCH₃ H C₂H₅ C(CH₃)₃ 1140. OCH₃ H CF₃ C(CH₃)₃ 1141.OCH₃ H OCF₃ C(CH₃)₃ 1142. OCH₃ H OCHF₂ C(CH₃)₃ 1143. OCH₃ H Br C₆H₅1144. OCH₃ H OCH₃ C₆H₅ 1145. OCH₃ H Cl C₆H₅ 1146. OCH₃ H F C₆H₅ 1147.OCH₃ H CH₃ C₆H₅ 1148. OCH₃ H C₂H₅ C₆H₅ 1149. OCH₃ H CF₃ C₆H₅ 1150. OCH₃H OCF₃ C₆H₅ 1151. OCH₃ H OCHF₂ C₆H₅ 1152. OCH₃ H Br cyclopropyl 1153.OCH₃ H OCH₃ cyclopropyl 1154. OCH₃ H Cl cyclopropyl 1155. OCH₃ H Fcyclopropyl 1156. OCH₃ H CH₃ cyclopropyl 1157. OCH₃ H C₂H₅ cyclopropyl1158. OCH₃ H CF₃ cyclopropyl 1159. OCH₃ H OCF₃ cyclopropyl 1160. OCH₃ HOCHF₂ cyclopropyl 1161. OCH₃ H Br CH₂-cyclopropyl 1162. OCH₃ H OCH₃CH₂-cyclopropyl 1163. OCH₃ H Cl CH₂-cyclopropyl 1164. OCH₃ H FCH₂-cyclopropyl 1165. OCH₃ H CH₃ CH₂-cyclopropyl 1166. OCH₃ H C₂H₅CH₂-cyclopropyl 1167. OCH₃ H CF₃ CH₂-cyclopropyl 1168. OCH₃ H OCF₃CH₂-cyclopropyl 1169. OCH₃ H OCHF₂ CH₂-cyclopropyl 1170. OCH₃ H Brcyclobutyl 1171. OCH₃ H OCH₃ cyclobutyl 1172. OCH₃ H Cl cyclobutyl 1173.OCH₃ H F cyclobutyl 1174. OCH₃ H CH₃ cyclobutyl 1175. OCH₃ H C₂H₅cyclobutyl 1176. OCH₃ H CF₃ cyclobutyl 1177. OCH₃ H OCF₃ cyclobutyl1178. OCH₃ H OCHF₂ cyclobutyl 1179. OCH₃ H Br cyclopentyl 1180. OCH₃ HOCH₃ cyclopentyl 1181. OCH₃ H Cl cyclopentyl 1182. OCH₃ H F cyclopentyl1183. OCH₃ H CH₃ cyclopentyl 1184. OCH₃ H C₂H₅ cyclopentyl 1185. OCH₃ HCF₃ cyclopentyl 1186. OCH₃ H OCF₃ cyclopentyl 1187. OCH₃ H OCHF₂cyclopentyl 1188. OCH₃ H Br cyclohexyl 1189. OCH₃ H OCH₃ cyclohexyl1190. OCH₃ H Cl cyclohexyl 1191. OCH₃ H F cyclohexyl 1192. OCH₃ H CH₃cyclohexyl 1193. OCH₃ H C₂H₅ cyclohexyl 1194. OCH₃ H CF₃ cyclohexyl1195. OCH₃ H OCF₃ cyclohexyl 1196. OCH₃ H OCHF₂ cyclohexyl 1197. Cl Cl HH 1198. Cl F H H 1199. Cl CH₃ H H 1200. Cl OCH₃ H H 1201. Cl Br H H1202. Cl CF₃ H H 1203. Cl OCF₃ H H 1204. Cl Cl H CH₃ 1205. Cl F H CH₃1206. Cl CH₃ H CH₃ 1207. Cl OCH₃ H CH₃ 1208. Cl Br H CH₃ 1209. Cl CF₃ HCH₃ 1210. Cl OCF₃ H CH₃ 1211. Cl Cl H C₂H₅ 1212. Cl F H C₂H₅ 1213. ClCH₃ H C₂H₅ 1214. Cl OCH₃ H C₂H₅ 1215. Cl Br H C₂H₅ 1216. Cl CF₃ H C₂H₅1217. Cl OCF₃ H C₂H₅ 1218. Cl Cl H n-C₃H₇ 1219. Cl F H n-C₃H₇ 1220. ClCH₃ H n-C₃H₇ 1221. Cl OCH₃ H n-C₃H₇ 1222. Cl Br H n-C₃H₇ 1223. Cl CF₃ Hn-C₃H₇ 1224. Cl OCF₃ H n-C₃H₇ 1225. Cl Cl H CH(CH₃)₂ 1226. Cl F HCH(CH₃)₂ 1227. Cl CH₃ H CH(CH₃)₂ 1228. Cl OCH₃ H CH(CH₃)₂ 1229. Cl Br HCH(CH₃)₂ 1230. Cl CF₃ H CH(CH₃)₂ 1231. Cl OCF₃ H CH(CH₃)₂ 1232. Cl Cl Hn-C₄H₉ 1233. Cl F H n-C₄H₉ 1234. Cl CH₃ H n-C₄H₉ 1235. Cl OCH₃ H n-C₄H₉1236. Cl Br H n-C₄H₉ 1237. Cl CF₃ H n-C₄H₉ 1238. Cl OCF₃ H n-C₄H₉ 1239.Cl Cl H C(CH₃)₃ 1240. Cl F H C(CH₃)₃ 1241. Cl CH₃ H C(CH₃)₃ 1242. ClOCH₃ H C(CH₃)₃ 1243. Cl Br H C(CH₃)₃ 1244. Cl CF₃ H C(CH₃)₃ 1245. ClOCF₃ H C(CH₃)₃ 1246. Cl Cl H C₆H₅ 1247. Cl F H C₆H₅ 1248. Cl CH₃ H C₆H₅1249. Cl OCH₃ H C₆H₅ 1250. Cl Br H C₆H₅ 1251. Cl CF₃ H C₆H₅ 1252. ClOCF₃ H C₆H₅ 1253. Cl Cl H cyclopropyl 1254. Cl F H cyclopropyl 1255. ClCH₃ H cyclopropyl 1256. Cl OCH₃ H cyclopropyl 1257. Cl Br H cyclopropyl1258. Cl CF₃ H cyclopropyl 1259. Cl OCF₃ H cyclopropyl 1260. Cl Cl HCH₂-cyclopropyl 1261. Cl F H CH₂-cyclopropyl 1262. Cl CH₃ HCH₂-cyclopropyl 1263. Cl OCH₃ H CH₂-cyclopropyl 1264. Cl Br HCH₂-cyclopropyl 1265. Cl CF₃ H CH₂-cyclopropyl 1266. Cl OCF₃ HCH₂-cyclopropyl 1267. Cl Cl H cyclobutyl 1268. Cl F H cyclobutyl 1269.Cl CH₃ H cyclobutyl 1270. Cl OCH₃ H cyclobutyl 1271. Cl Br H cyclobutyl1272. Cl CF₃ H cyclobutyl 1273. Cl OCF₃ H cyclobutyl 1274. Cl Cl Hcyclopentyl 1275. Cl F H cyclopentyl 1276. Cl CH₃ H cyclopentyl 1277. ClOCH₃ H cyclopentyl 1278. Cl Br H cyclopentyl 1279. Cl CF₃ H cyclopentyl1280. Cl OCF₃ H cyclopentyl 1281. Cl Cl H cyclohexyl 1282. Cl F Hcyclohexyl 1283. Cl CH₃ H cyclohexyl 1284. Cl OCH₃ H cyclohexyl 1285. ClBr H cyclohexyl 1286. Cl CF₃ H cyclohexyl 1287. Cl OCF₃ H cyclohexyl1288. Cl H Cl H 1289. Cl H F H 1290. Cl H CH₃ H 1291. Cl H OCH₃ H 1292.Cl H Br H 1293. Cl H CF₃ H 1294. Cl H OCF₃ H 1295. Cl H Cl CH₃ 1296. ClH F CH₃ 1297. Cl H CH₃ CH₃ 1298. Cl H OCH₃ CH₃ 1299. Cl H Br CH₃ 1300.Cl H CF₃ CH₃ 1301. Cl H OCF₃ CH₃ 1302. Cl H Cl C₂H₅ 1303. Cl H F C₂H₅1304. Cl H CH₃ C₂H₅ 1305. Cl H OCH₃ C₂H₅ 1306. Cl H Br C₂H₅ 1307. Cl HCF₃ C₂H₅ 1308. Cl H OCF₃ C₂H₅ 1309. Cl H Cl n-C₃H₇ 1310. Cl H F n-C₃H₇1311. Cl H CH₃ n-C₃H₇ 1312. Cl H OCH₃ n-C₃H₇ 1313. Cl H Br n-C₃H₇ 1314.Cl H CF₃ n-C₃H₇ 1315. Cl H OCF₃ n-C₃H₇ 1316. Cl H Cl CH(CH₃)₂ 1317. Cl HF CH(CH₃)₂ 1318. Cl H CH₃ CH(CH₃)₂ 1319. Cl H OCH₃ CH(CH₃)₂ 1320. Cl HBr CH(CH₃)₂ 1321. Cl H CF₃ CH(CH₃)₂ 1322. Cl H OCF₃ CH(CH₃)₂ 1323. Cl HCl n-C₄H₉ 1324. Cl H F n-C₄H₉ 1325. Cl H CH₃ n-C₄H₉ 1326. Cl H OCH₃n-C₄H₉ 1327. Cl H Br n-C₄H₉ 1328. Cl H CF₃ n-C₄H₉ 1329. Cl H OCF₃ n-C₄H₉1330. Cl H Cl C(CH₃)₃ 1331. Cl H F C(CH₃)₃ 1332. Cl H CH₃ C(CH₃)₃ 1333.Cl H OCH₃ C(CH₃)₃ 1334. Cl H Br C(CH₃)₃ 1335. Cl H CF₃ C(CH₃)₃ 1336. ClH OCF₃ C(CH₃)₃ 1337. Cl. H Cl C₆H₅ 1338. Cl H F C₆H₅ 1339. Cl H CH₃ C₆H₅1340. Cl H OCH₃ C₆H₅ 1341. Cl H Br C₆H₅ 1342. Cl H CF₃ C₆H₅ 1343. Cl HOCF₃ C₆H₅ 1344. Cl H Cl cyclopropyl 1345. Cl H F cyclopropyl 1346. Cl HCH₃ cyclopropyl 1347. Cl H OCH₃ cyclopropyl 1348. Cl H Br cyclopropyl1349. Cl H CF₃ cyclopropyl 1350. Cl H OCF₃ cyclopropyl 1351. Cl H ClCH₂-cyclopropyl 1352. Cl H F CH₂-cyclopropyl 1353. Cl H CH₃CH₂-cyclopropyl 1354. Cl H OCH₃ CH₂-cyclopropyl 1355. Cl H BrCH₂-cyclopropyl 1356. Cl H CF₃ CH₂-cyclopropyl 1357. Cl H OCF₃CH₂-cyclopropyl 1358. Cl H Cl cyclobutyl 1359. Cl H F cyclobutyl 1360.Cl H CH₃ cyclobutyl 1361. Cl H OCH₃ cyclobutyl 1362. Cl H Br cyclobutyl1363. Cl H CF₃ cyclobutyl 1364. Cl H OCF₃ cyclobutyl 1365. Cl H Clcyclopentyl 1366. Cl H F cyclopentyl 1367. Cl H CH₃ cyclopentyl 1368. ClH OCH₃ cyclopentyl 1369. Cl H Br cyclopentyl 1370. Cl H CF₃ cyclopentyl1371. Cl H OCF₃ cyclopentyl 1372. Cl H Cl cyclohexyl 1373. Cl H Fcyclohexyl 1374. Cl H CH₃ cyclohexyl 1375. Cl H OCH₃ cyclohexyl 1376. ClH Br cyclohexyl 1377. Cl H CF₃ cyclohexyl 1378. Cl H OCF₃ cyclohexyl1379. Br Cl H H 1380. Br F H H 1381. Br CH₃ H H 1382. Br OCH₃ H H 1383.Br Br H H 1384. Br CF₃ H H 1385. Br OCF₃ H H 1386. Br Cl H CH₃ 1387. BrF H CH₃ 1388. Br CH₃ H CH₃ 1389. Br OCH₃ H CH₃ 1390. Br Br H CH₃ 1391.Br CF₃ H CH₃ 1392. Br OCF₃ H CH₃ 1393. Br Cl H C₂H₅ 1394. Br F H C₂H₅1395. Br CH₃ H C₂H₅ 1396. Br OCH₃ H C₂H₅ 1397. Br Br H C₂H₅ 1398. Br CF₃H C₂H₅ 1399. Br OCF₃ H C₂H₅ 1400. Br Cl H n-C₃H₇ 1401. Br F H n-C₃H₇1402. Br CH₃ H n-C₃H₇ 1403. Br OCH₃ H n-C₃H₇ 1404. Br Br H n-C₃H₇ 1405.Br CF₃ H n-C₃H₇ 1406. Br OCF₃ H n-C₃H₇ 1407. Br Cl H CH(CH₃)₂ 1408. Br FH CH(CH₃)₂ 1409. Br CH₃ H CH(CH₃)₂ 1410. Br OCH₃ H CH(CH₃)₂ 1411. Br BrH CH(CH₃)₂ 1412. Br CF₃ H CH(CH₃)₂ 1413. Br OCF₃ H CH(CH₃)₂ 1414. Br ClH n-C₄H₉ 1415. Br F H n-C₄H₉ 1416. Br CH₃ H n-C₄H₉ 1417. Br OCH₃ Hn-C₄H₉ 1418. Br Br H n-C₄H₉ 1419. Br CF₃ H n-C₄H₉ 1420. Br OCF₃ H n-C₄H₉1421. Br Cl H C(CH₃)₃ 1422. Br F H C(CH₃)₃ 1423. Br CH₃ H C(CH₃)₃ 1424.Br OCH₃ H C(CH₃)₃ 1425. Br Br H C(CH₃)₃ 1426. Br CF₃ H C(CH₃)₃ 1427. BrOCF₃ H C(CH₃)₃ 1428. Br Cl H C₆H₅ 1429. Br F H C₆H₅ 1430. Br CH₃ H C₆H₅1431. Br OCH₃ H C₆H₅ 1432. Br Br H C₆H₅ 1433. Br CF₃ H C₆H₅ 1434. BrOCF₃ H C₆H₅ 1435. Br Cl H cyclopropyl 1436. Br F H cyclopropyl 1437. BrCH₃ H cyclopropyl 1438. Br OCH₃ H cyclopropyl 1439. Br Br H cyclopropyl1440. Br CF₃ H cyclopropyl 1441. Br OCF₃ H cyclopropyl 1442. Br Cl HCH₂-cyclopropyl 1443. Br F H CH₂-cyclopropyl 1444. Br CH₃ HCH₂-cyclopropyl 1445. Br OCH₃ H CH₂-cyclopropyl 1446. Br Br HCH₂-cyclopropyl 1447. Br CF₃ H CH₂-cyclopropyl 1448. Br OCF₃ HCH₂-cyclopropyl 1449. Br Cl H cyclobutyl 1450. Br F H cyclobutyl 1451.Br CH₃ H cyclobutyl 1452. Br OCH₃ H cyclobutyl 1453. Br Br H cyclobutyl1454. Br CF₃ H cyclobutyl 1455. Br OCF₃ H cyclobutyl 1456. Br Cl Hcyclopentyl 1457. Br F H cyclopentyl 1458. Br CH₃ H cyclopentyl 1459. BrOCH₃ H cyclopentyl 1460. Br Br H cyclopentyl 1461. Br CF₃ H cyclopentyl1462. Br OCF₃ H cyclopentyl 1463. Br Cl H cyclohexyl 1464. Br F Hcyclohexyl 1465. Br CH₃ H cyclohexyl 1466. Br OCH₃ H cyclohexyl 1467. BrBr H cyclohexyl 1468. Br CF₃ H cyclohexyl 1469. Br 00F₃ H cyclohexyl1470. Br H Cl H 1471. Br H F H 1472. Br H CH₃ H 1473. Br H OCH₃ H 1474.Br H Br H 1475. Br H CF₃ H 1476. Br H OCF₃ H 1477. Br H Cl CH₃ 1478. BrH F CH₃ 1479. Br H CH₃ CH₃ 1480. Br H OCH₃ CH₃ 1481. Br H Br CH₃ 1482.Br H CF₃ CH₃ 1483. Br H OCF₃ CH₃ 1484. Br H Cl C₂H₅ 1485. Br H F C₂H₅1486. Br H CH₃ C₂H₅ 1487. Br H OCH₃ C₂H₅ 1488. Br. H Br C₂H₅ 1489. Br HCF₃ C₂H₅ 1490. Br H OCF₃ C₂H₅ 1491. Br H Cl n-C₃H₇ 1492. Br H F n-C₃H₇1493. Br H CH₃ n-C₃H₇ 1494. Br H OCH3 n-C₃H₇ 1495. Br H Br n-C₃H₇ 1496.Br H CF₃ n-C₃H₇ 1497. Br H OCF₃ n-C₃H₇ 1498. Br H Cl CH(CH₃)₂ 1499. Br HF CH(CH₃)₂ 1500. Br H CH₃ CH(CH₃)₂ 1501. Br H OCH₃ CH(CH₃)₂ 1502. Br HBr CH(CH₃)₂ 1503. Br H CF₃ CH(CH₃)₂ 1504. Br H OCF₃ CH(CH₃)₂ 1505. Br HCl n-C₄H₉ 1506. Br H F n-C₄H₉ 1507. Br H CH₃ n-C₄H₉ 1508. Br H OCH₃n-C₄H₉ 1509. Br H Br n-C₄H₉ 1510. Br H CF₃ n-C₄H₉ 1511. Br H OCF₃ n-C₄H₉1512. Br H Cl C(CH₃)₃ 1513. Br H F C(CH₃)₃ 1514. Br H CH₃ C(CH₃)₃ 1515.Br H OCH₃ C(CH₃)₃ 1516. Br H Br C(CH₃)₃ 1517. Br H CF₃ C(CH₃)₃ 1518. BrH OCF₃ C(CH₃)₃ 1519. Br H Cl C₆H₅ 1520. Br H F C₆H₅ 1521. Br H CH₃ C₆H₅1522. Br H OCH₃ C₆H₅ 1523. Br H Br C₆H₅ 1524. Br H CF₃ C₆H₅ 1525. Br HOCF₃ C₆H₅ 1526. Br H Cl cyclopropyl 1527. Br H F cyclopropyl 1528. Br HCH₃ cyclopropyl 1529. Br H OCH₃ cyclopropyl 1530. Br H Br cyclopropyl1531. Br H CF₃ cyclopropyl 1532. Br H OCF₃ cyclopropyl 1533. Br H ClCH₂-cyclopropyl 1534. Br H F CH₂-cyclopropyl 1535. Br H CH₃CH₂-cyclopropyl 1536. Br H OCH₃ CH₂-cyclopropyl 1537. Br H BrCH₂-cyclopropyl 1538. Br H CF₃ CH₂-cyclopropyl 1539. Br H OCF₃CH₂-cyclopropyl 1540. Br H Cl cyclobutyl 1541 Br H F cyclobutyl 1542. BrH CH₃ cyclobutyl 1543. Br H OCH₃ cyclobutyl 1544. Br H Br cyclobutyl1545. Br H CF₃ cyclobutyl 1546. Br H OCF₃ cyclobutyl 1547. Br H Clcyclopentyl 1548. Br H F cyclopentyl 1549. Br H CH₃ cyclopentyl 1550. BrH OCH₃ cyclopentyl 1551. Br H Br cyclopentyl 1552. Br H CF₃ cyclopentyl1553. Br H OCF₃ cyclopentyl 1554. Br H Cl cyclohexyl 1555. Br H Fcyclohexyl 1556. Br H CH₃ cyclohexyl 1557. Br H OCH₃ cyclohexyl 1558. BrH Br cyclohexyl 1559. Br H CF₃ cyclohexyl 1560. Br H OCF₃ cyclohexyl1561. CH₃ Cl H H 1562. CH₃ F H H 1563. CH₃ CH₃ H H 1564. CH₃ OCH₃ H H1565. CH₃ Br H H 1566. CH₃ CF₃ H H 1567. CH₃ OCF₃ H H 1568. CH₃ Cl H CH₃1569. CH₃ F H CH₃ 1570. CH₃ CH₃ H CH₃ 1571. CH₃ Br H CH₃ 1572. CH₃ CF₃ HCH₃ 1573. CH₃ OCF₃ H CH₃ 1574. CH₃ Cl H C₂H₅ 1575. CH₃ F H C₂H₅ 1576.CH₃ CH₃ H C₂H₅ 1577. CH₃ Br H C₂H₅ 1578. CH₃ CF₃ H C₂H₅ 1579. CH₃ OCF₃ HC₂H₅ 1580. CH₃ Cl H n-C₃H₇ 1581. CH₃ F H n-C₃H₇ 1582. CH₃ CH₃ H n-C₃H₇1583. CH₃ Br H n-C₃H₇ 1584. CH₃ CF₃ H n-C₃H₇ 1585. CH₃ OCF₃ H n-C₃H₇1586. CH₃ Cl H CH(CH₃)₂ 1587. CH₃ F H CH(CH₃)₂ 1588. CH₃ CH₃ H CH(CH₃)₂1589. CH₃ Br H CH(CH₃)₂ 1590. CH₃ CF₃ H CH(CH₃)₂ 1591. CH₃ OCF₃ HCH(CH₃)₂ 1592. CH₃ Cl H n-C₄H₉ 1593. CH₃ F H n-C₄H₉ 1594. CH₃ CH₃ Hn-C₄H₉ 1595. CH₃ Br H n-C₄H₉ 1596. CH₃ CF₃ H n-C₄H₉ 1597. CH₃ OCF₃ Hn-C₄H₉ 1598. CH₃ Cl H C(CH₃)₃ 1599. CH₃ F H C(CH₃)₃ 1600. CH₃ CH₃ HC(CH₃)₃ 1601. CH₃ Br H C(CH₃)₃ 1602. CH₃ CF₃ H C(CH₃)₃ 1603. CH₃ OCF₃ HC(CH₃)₃ 1604. CH₃ Cl H C₆H₅ 1605. CH₃ F H C₆H₅ 1606. CH₃ CH₃ H C₆H₅1607. CH₃ Br H C₆H₅ 1608. CH₃ CF₃ H C₆H₅ 1609. CH₃ OCF₃ H C₆H₅ 1610. CH₃Cl H cyclopropyl 1611. CH₃ F H cyclopropyl 1612. CH₃ CH₃ H cyclopropyl1613. CH₃ Br H cyclopropyl 1614. CH₃ CF₃ H cyclopropyl 1615. CH₃ OCF₃ Hcyclopropyl 1616. CH₃ Cl H CH₂-cyclopropyl 1617. CH₃ F H CH₂-cyclopropyl1618. CH₃ CH₃ H CH₂-cyclopropyl 1619. CH₃ Br H CH₂-cyclopropyl 1620. CH₃CF₃ H CH₂-cyclopropyl 1621. CH₃ OCF₃ H CH₂-cyclopropyl 1622. CH₃ Cl Hcyclobutyl 1623. CH₃ F H cyclobutyl 1624. CH₃ CH₃ H cyclobutyl 1625. CH₃Br H cyclobutyl 1626. CH₃ CF₃ H cyclobutyl 1627. CH₃ OCF₃ H cyclobutyl1628. CH₃ Cl H cyclopentyl 1629. CH₃ F H cyclopentyl 1630. CH₃ CH₃ Hcyclopentyl 1631. CH₃ Br H cyclopentyl 1632. CH₃ CF₃ H cyclopentyl 1633.CH₃ OCF₃ H cyclopentyl 1634. CH₃ Cl H cyclohexyl 1635. CH₃ F Hcyclohexyl 1636. CH₃ CH₃ H cyclohexyl 1637. CH₃ Br H cyclohexyl 1638.CH₃ CF₃ H cyclohexyl 1639. CH₃ OCF₃ H cyclohexyl 1640. CH₃ H Cl H 1641.CH₃ H F H 1642. CH₃ H CH₃ H 1643. CH₃ H Br H 1644. CH₃ H CF₃ H 1645. CH₃H OCF₃ H 1646. CH₃ H Cl CH₃ 1647. CH₃ H F CH₃ 1648. CH₃ H CH₃ CH₃ 1649.CH₃ H Br CH₃ 1650. CH₃ H CF₃ CH₃ 1651. CH₃ H OCF₃ CH₃ 1652. CH₃ H ClC₂H₅ 1653. CH₃ H F C₂H₅ 1654. CH₃ H CH₃ C₂H₅ 1655. CH₃ H Br C₂H₅ 1656.CH₃ H CF₃ C₂H₅ 1657. CH₃ H OCF₃ C₂H₅ 1658. CH₃ H Cl n-C₃H₇ 1659. CH₃ H Fn-C₃H₇ 1660. CH₃ H CH₃ n-C₃H₇ 1661. CH₃ H Br n-C₃H₇ 1662. CH₃ H CF₃n-C₃H₇ 1663. CH₃ H OCF₃ n-C₃H₇ 1664. CH₃ H Cl CH(CH₃)₂ 1665. CH₃ H FCH(CH₃)₂ 1666. CH₃ H CH₃ CH(CH₃)₂ 1667. CH₃ H Br CH(CH₃)₂ 1668. CH₃ HCF₃ CH(CH₃)₂ 1669. CH₃ H OCF₃ CH(CH₃)₂ 1670. CH₃ H Cl n-C₄H₉ 1671. CH₃ HF n-C₄H₉ 1672. CH₃ H CH₃ n-C₄H₉ 1673. CH₃ H Br n-C₄H₉ 1674. CH₃ H CF₃n-C₄H₉ 1675. CH₃ H OCF₃ n-C₄H₉ 1676. CH₃ H Cl C(CH₃)₃ 1677. CH₃ H FC(CH₃)₃ 1678. CH₃ H CH₃ C(CH₃)₃ 1679. CH₃ H Br C(CH₃)₃ 1680. CH₃ H CF₃C(CH₃)₃ 1681. CH₃ H OCF₃ C(CH₃)₃ 1682. CH₃ H Cl C₆H₅ 1683. CH₃ H F C₆H₅1684. CH₃ H CH₃ C₆H₅ 1685. CH₃ H Br C₆H₅ 1686. CH₃ H CF₃ C₆H₅ 1687. CH₃H OCF₃ C₆H₅ 1688. CH₃ H Cl cyclopropyl 1689. CH₃ H F cyclopropyl 1690.CH₃ H CH₃ cyclopropyl 1691. CH₃ H Br cyclopropyl 1692. CH₃ H CF₃cyclopropyl 1693. CH₃ H OCF₃ cyclopropyl 1694. CH₃ H Cl CH₂-cyclopropyl1695. CH₃ H F CH₂-cyclopropyl 1696. CH₃ H CH₃ CH₂-cyclopropyl 1697. CH₃H Br CH₂-cyclopropyl 1698. CH₃ H CF₃ CH₂-cyclopropyl 1699. CH₃ H OCF₃CH₂-cyclopropyl 1700. CH₃ H Cl cyclobutyl 1701. CH₃ H F cyclobutyl 1702.CH₃ H CH₃ cyclobutyl 1703. CH₃ H Br cyclobutyl 1704. CH₃ H CF₃cyclobutyl 1705. CH₃ H OCF₃ cyclobutyl 1706. CH₃ H Cl cyclopentyl 1707.CH₃ H F cyclopentyl 1708. CH₃ H CH₃ cyclopentyl 1709. CH₃ H Brcyclopentyl 1710. CH₃ H CF₃ cyclopentyl 1711. CH₃ H OCF₃ cyclopentyl1712. CH₃ H Cl cyclohexyl 1713. CH₃ H F cyclohexyl 1714. CH₃ H CH₃cyclohexyl 1715. CH₃ H Br cyclohexyl 1716. CH₃ H CF₃ cyclohexyl 1717.CH₃ H OCF₃ cyclohexyl

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ib (≡I whereR^(a)═R^(e)═H, X═O, Y═O, R¹═H, R³═H and n=0) where R^(b), R^(c), R^(d)and R² have the meanings given above, in particular the meaningsmentioned as being preferred. Examples of such compounds are thecompounds Ib.1 to Ib.1717 in which the variables R^(b), R^(c), R^(d) andR² together have the meanings given in one row of Table 1.

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ic (≡I whereR^(a)═R^(e)═H, X═O, Y═O, R¹═H, R³═C₂H₅ and n=0) where R^(b), R^(c),R^(d) and R² have the meanings given above, in particular the meaningsmentioned as being preferred. Examples of such compounds are thecompounds Ic.1 to Ic.1717 in which the variables R^(b), R^(c), R^(d) andR² together have the meanings given in one row of Table 1.

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula Id (≡I where X═O,Y═O, R¹═H, R³═CH(CH₃)₂ and n=0) where R^(b), R^(c), R^(d) and R² havethe meanings given above, in particular the meanings mentioned as beingpreferred. Examples of such compounds are the compounds Id.1 to Id.1717in which the variables R^(b), R^(c), R^(d) and R² together have themeanings given in one row of Table 1.

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ie (≡I where X═O,Y═O, R¹═H, R³═H, A═O and n=1) where R^(b), R^(c), R^(d) and R² have themeanings given above, in particular the meanings mentioned as beingpreferred. Examples of such compounds are the compounds Ie.1 to Ie.1717in which the variables R^(b), R^(c), R^(d) and R² together have themeanings given in one row of Table 1.

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula If (≡I where X═O,Y═O, R¹═H, R³═CH₃, A═O and n=1) where R^(b), R^(c), R^(d) and R² havethe meanings given above, in particular the meanings mentioned as beingpreferred. Examples of such compounds are the compounds If.1 to If.1717in which the variables R^(b), R^(c), R^(d) and R² together have themeanings given in one row of Table 1.

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ig (≡I where X═O,Y═O, R¹═H, R³ ═C₂H₅, A═O and n=1) where R^(b), R^(c), R^(d) and R² havethe meanings given above, in particular the meanings mentioned as beingpreferred. Examples of such compounds are the compounds Ig.1 to Ig.1717in which the variables R^(b), R^(c), R^(d) and R² together have themeanings given in one row of Table 1.

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ih (≡I where X═O,Y═O, R¹H, R³═CH(CH₃)₂, A═O and n=1) where R^(b), R^(c), R^(d) and R²have the meanings given above, in particular the meanings mentioned asbeing preferred. Examples of such compounds are the compounds Ih.1 toIh.1717 in which the variables R^(b), R^(c), R^(d) and R² together havethe meanings given in one row of Table 1.

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ii (≡I where X═O,Y═O, R¹═H, R³═H, n=1 and A═NR¹² where R¹²═H) where R^(b), R^(c), R^(d)and R² have the meanings given above, in particular the meaningsmentioned as being preferred. Examples of such compounds are thecompounds Ii.1 to Ii.1717 in which the variables R^(b), R^(c), R^(d) andR² together have the meanings given in one row of Table 1.

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ij (≡I where X═O,Y═O, R¹═H, R³═CH₃, n=1 and A═NR¹² where R¹²═H) where R^(b), R^(c), R^(d)and R² have the meanings given above, in particular the meaningsmentioned as being preferred. Examples of such compounds are thecompounds Ij.1 to Ij.1717 in which the variables R^(b), R^(c), R^(d) andR² together have the meanings given in one row of Table 1.

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ik (≡I where X═O,Y═O, R¹═H, R³═C₂H₅, n=1 and A═NR¹² where R¹²═H) where R^(b), R^(c),R^(d) and R² have the meanings given above, in particular the meaningsmentioned as being preferred. Examples of such compounds are thecompounds Ik.1 to Ik.1717 in which the variables R^(b), R^(c), R^(d) andR² together have the meanings given in one row of Table 1.

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula II (≡I where X═O,Y═O, R¹═H, R³═CH(CH₃)₂, n=1 and A═NR¹² where R¹²═H) where R^(b), R^(c),R^(d) and R² have the meanings given above, in particular the meaningsmentioned as being preferred. Examples of such compounds are thecompounds Il.1 to Il.1717 in which the variables R^(b), R^(c), R^(d) andR² together have the meanings given in one row of Table 1.

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula Im (≡I where X═O,Y═O, R¹═H, R³═H, n=1 and A═NR¹² where R¹²═CH₃) where R^(b), R^(c), R^(d)and R² have the meanings given above, in particular the meaningsmentioned as being preferred. Examples of such compounds are thecompounds Im.1 to Im.1717 in which the variables R^(b), R^(c), R^(d) andR² together have the meanings given in one row of Table 1.

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula In (≡I where X═O,Y═O, R¹═H, R³═CH₃, n=1 and A═NR¹² where R¹²═CH₃) where R^(b), R^(c),R^(d) and R² have the meanings given above, in particular the meaningsmentioned as being preferred. Examples of such compounds are thecompounds In.1 to In.1717 in which the variables R^(b), R^(c), R^(d) andR² together have the meanings given in one row of Table 1.

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula Io (≡I where X═O,Y═O, R¹═H, R³═C₂H₅, n=1 and A═NR¹² where R¹²═CH₃) where R^(b), R^(c),R^(d) and R² have the meanings given above, in particular the meaningsmentioned as being preferred. Examples of such compounds are thecompounds Io.1 to Io.1717 in which the variables R^(b), R^(c), R^(d) andR² together have the meanings given in one row of Table 1.

Particular preference is also given to the1-phenylpyrrolidin-2-one-3-carboxamides of the formula Ip (≡I where X═O,Y═O, R¹═H, R³═CH(CH₃)₂, n=1 and A═NR¹² where R¹²═CH₃) where R^(b),R^(c), R^(d) and R² have the meanings given above, in particular themeanings mentioned as being preferred. Examples of such compounds arethe compounds Ip.1 to Ip.1717 in which the variables R^(b), R^(c), R^(d)and R² together have the meanings given in one row of Table 1.

The 1-phenylpyrrolidin-2-one-3-carboxamides of the formula I accordingto the invention can be prepared, for example, by one of the processes Ato G described below.

A) Amidation of a Carboxylic Acid II or a Carboxylic Acid Derivative ofII

The preparation of the compound I according to the invention can becarried out, for example, according to Scheme 1 by reacting an activatedform of a pyrrolidine-3-carboxylic acid of the formula II with an amineIII.

In Scheme 1, the variables R¹, X, R^(a), R^(b), R^(c), R^(d), R^(e), A,n, R² and R³ are as defined above. Such reactions are known, for examplefrom WO 01/83459, and can be applied in an analogous manner to thereaction illustrated in Scheme 1. The carboxylic acid II is preferablyinitially activated by carrying out the reaction in the presence of acoupling agent. Suitable coupling agents are, for example,N,N′-carbonyldiimidazole or carbodiimides, such asdicyclohexylcarbodiimide. These compounds are generally employed in anat least equimolar amount and up to a four-fold excess, based on thecarboxylic acid II. If appropriate, it may be advantageous to carry outthe reaction of the carboxylic acid II with the coupling agent in thepresence of a catalytic amount of a tertiary aminopyridine, such as4-dimethylaminopyridine (DMAP). In this case, the amount ofaminopyridine added is preferably 5 to 10 mol %, based on the carboxylicacid II. The reaction is usually carried out in a solvent. Suitablesolvents are, for example, chlorinated hydrocarbons, such as methylenechloride, 1,2-dichloroethane, ethers, for example dialkyl ethers, suchas diethyl ether, methyl tert-butyl ether, or cyclic ethers, such astetrahydrofuran or dioxane, carboxamides, such as dimethylformamide,N-methyllactams, such as N-methylpyrrolidone, nitriles, such asacetonitrile, aromatic hydrocarbons, such as toluene, or mixtures ofthese.

The molar ratio of amine III to carboxylic acid II is generally at least0.9:1, preferably at least 1:1. If appropriate, it may be advantageousto employ the amine in a slight excess, for example in an excess of upto 30%, based on the carboxylic acid II.

In general, the reaction temperature is in the range from 0° C. to theboiling point of the solvent.

Alternatively, the carboxylic acid II can initially be activated byconverting it into its acid halide, preferably its acid chloride. Meansfor this purpose are known, for example from U.S. Pat. No. 4,874,422.Suitable compounds are inorganic acid halides, preferably acidchlorides, such as thionyl chloride, phosphoryl chloride phosphoruspentachloride or phosphorus trichloride, and organic acid chlorides,such as oxalyl chloride. The acid halide of II formed can be isolatedand then be reacted with the amine III. It is also possible to react theacid chloride of II formed directly, without isolation, with the amineIII. If appropriate, the reactivity of the acid halide is enhanced byadding catalytic amounts of an N,N-dialkylcarboxamide, such asdimethylformamide. The halogenating agent is usually employed in an atleast equimolar amount, based on the carboxylic acid II. The acidhalides thionyl chloride, phosphorus trichloride or phosphoryl chloridecan simultaneously act as solvent. Suitable solvents arefurthermore-solvents which are inert under the reaction conditions, forexample chlorinated hydrocarbons, such as methylene chloride,1,2-dichloroethane, aromatic hydrocarbons, such as benzene or toluene,aliphatic and cycloaliphatic hydrocarbons, such as hexane, petroleumether, cyclohexane, and mixtures thereof. The reaction temperature isgenerally between room temperature and the boiling point of the solvent.After the reaction has ended, excess halogenating agent is generallyremoved. The resulting acid halide of II is then reacted with the amineIII. In general, the amine III is dissolved in the solvent which wasalso used for preparing the carbonyl halide, unless the solvent is oneof the acid halides mentioned above.

If appropriate, the reaction is carried out in the presence of anauxiliary base which is preferably employed in an equimolar amount or anup to four-fold excess, based on the carboxylic acid II. Suitable basesare, for example, amines such as 1,5-diazabicyclo[4.3.0]non-5-ene (DBN),1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), pyridine, α-, β-, γ-lutidineor triethylamine.

It is, of course, also possible to use other methods for activating thecarboxylic acid II. Such methods are described in the prior art, forexample in J. Falbe, Houben Weyl, Methoden der Organischen Chemie[Methods of organic chemistry], Vol. E5, 4th Ed., 1985, p. 941 ff.

In a further process variant, the corresponding carboxylic acid ester ofII (carboxylic acid ester VI), in particular the C₁-C₄-alkyl ester of IIand especially the methyl or ethyl ester of II, is reacted with theamine III, if appropriate in the presence of a base. Regarding asuitable base, solvent and reaction temperatures, reference is made towhat was said above. The preparation of the carboxylic acid ester VI isdescribed below.

Compounds of the formula II where R¹═H can be prepared, for example,similarly to a process described in Journal of Heterocyclic Chemistry, 3(1966), 311. The synthesis is shown in Scheme 2.

In Scheme 2, the variables R^(a), R^(b), R^(c), R^(d), R^(e) are asdefined above and R is C₁-C₄-alkyl. The reaction of the aniline compoundIV with butyrolactone is usually carried out in the presence of aninorganic acid, such as sulfuric acid, phosphoric acid or hydrochloricacid, or in the presence of an organic acid, such as acetic acid. Thereaction can be carried out in the absence of a solvent or in thepresence of a solvent. Suitable solvents are all solvents which areinert under the reaction conditions. However, the reaction is preferablycarried out in the absence of a solvent. If the reaction is carried outin the absence of a solvent, the butyrolactone is employed in an excess,based on the aniline IV. The reaction temperatures are generally in therange of from 20° C. to the boiling point of the solvent.

In the next step, the resulting pyrrolidinone V is generally reactedwithout further purification, for example with a carbonate (RO)₂CO or asynthetic equivalent, such as a chloroformic ester. To this end, thepyrrolidinone V is generally initially converted into the correspondingenolate by treatment with a suitable base. Suitable bases include inparticular organolithium compounds, such as n-butyllithium,tert-butyllithium and phenyllithium, lithium amides, such as lithiumdiisopropylamide, and alkali metal hydrides, such as sodium hydride. Thereaction is generally carried out in an organic solvent. Suitablesolvents are inert solvents, such as aliphatic and cycloaliphatichydrocarbons, such as hexane, petroleum ether, cyclohexane, ethers, forexample dialkyl ethers, such as diethyl ether, methyl tert-butyl ether,or cyclic ethers, such as tetrahydrofuran or dioxane, and also mixturesof these. In general, the deprotonation of the compound V is carried outat low temperatures to about room temperature, preferably at about 0° C.To this end, the base is employed in an at least equimolar amount,preferably a 1.1- to 4-fold molar excess, based on the compound V.

The subsequent introduction of the alkoxycarbonyl group is carried out,for example, using a carbonic acid diester, such as dimethyl carbonateor diethyl carbonate. The carbonic acid diester and the enolate of thecompound V are usually employed in equimolar amounts. It is, of course,possible for one of the two reactants to be employed in a slight excess.The temperature required for the reaction is generally in the range offrom 0° C. to the boiling point of the solvent.

The carboxylic acid ester VI is then hydrolyzed by known methods (see,for example, Organikum, 17th Edition, VEB Deutscher Verlag derWissenschaften, 1988, p. 415) to give the carboxylic acid II. Thehydrolysis can be carried out either in acidic medium using strongmineral acids, such as concentrated hydrochloric acid or sulfuric acid,or organic acids, such as glacial acetic acid, or mixtures of these inthe presence of water, or in alkaline medium using bases, such as alkalimetal hydroxide, for example sodium hydroxide or potassium hydroxide, ifappropriate in the presence of water.

Suitable solvents both for acidic and basic hydrolysis of esters are,for example, ethers, for example dialkyl ethers, such as diethyl ether,methyl tert-butyl ether, or cyclic ethers, such as tetrahydrofuran ordioxane, alcohols, water and mixtures of these solvents. The reactiontemperature is usually between room temperature and the boiling point ofthe solvent.

The compounds II can furthermore be prepared by aminoethylation ofmalonic acid esters VII in which R¹ is as defined above and R isC₁-C₄-alkyl with phenylaziridines VII and subsequent hydrolysis. Thesynthesis is shown in Scheme 3 and can be carried out similarly to knownmethods as described, for example, in Archiv der Pharmazie (Weinheim)302(4) (1969), 253, Justus Liebigs Ann. Chem. 716 (1968), 121-126 or inAngew. Chem. 74, (1962), 694.

The reaction is generally carried out in the presence of LiH/LiI in asolvent. Suitable solvents include aromatic solvents, such as benzene,toluene or xylene. Frequently, the aziridine VII and the malonic acidester are employed in approximately equimolar amounts. It may beadvantageous to employ an excess of malonic acid ester VIII, preferablyan excess of up to 30%, based on the aziridine VII. The resulting esterVIa is then converted according to known methods by hydrolysis in acidicor alkaline medium into the corresponding carboxylic acids II. Withregard to ester hydrolysis, reference is made to what was said above.

Compounds of the formula II in which R¹ is H can furthermore be preparedsimilarly to a process described in JP 2000143624-A. To this end,anilines IV are reacted with 1,1-cyclopropanedicarboxylic acid. Thesynthesis route is shown in Scheme 4. The reaction is usually carriedout in water or in an aliphatic nitrile, such as acetonitrile, or inmixtures thereof with water, at temperatures between 40 and 100° C.

Compounds of the formula II in which R¹ is H can furthermore be obtainedsimilarly to processes described in J. Am. Chem. Soc. 97 (1975), 3239 orOrganic Synthesis 60, (1981), 66. The reaction of the aniline IV withthe dioxaspirooctanedione IX gives the carboxylic acid II. The synthesisroute is shown in Scheme 5.

B) Linking a Pyrrolidinone X to an Aromatic Compound XI

Compounds of the formula I can furthermore be prepared by reactingsuitably substituted pyrrolidinones X with aromatic compounds of theformula XI according to the synthesis shown in Scheme 6.

In Scheme 6, the variables R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X,Y, A, n, R¹, R² and R³ are as defined above. Z is halogen, preferablyfluorine, chlorine or bromine, or B(OH)₂, B(OR′)₂ or Sn(R′)₃. In theseradicals, R′ is aryl, such as phenyl, or C₁-C₁₀-alkyl.

The reaction is preferably carried out in a solvent, in particular apolar aprotic solvent, such as dimethylformamide, dimethyl sulfoxide,N-methylpyrrolidone, dimethylacetamide, an ether, such as diethyl ether,tetrahydrofuran or dioxane, and mixtures of these solvents.

In general, the reaction is carried out at temperatures above roomtemperature, preferably in the range from 50 to 200° C. To this end, thecompounds of the formulae X and XI are preferably employed inapproximately equimolar amounts. It is, of course, also possible to usean excess of one of the components, the excess preferably being not morethan 50 mol %, in particular not more than 20 mol %, based on thecomponent which is present in a substoichiometric amount.

The compounds I according to the invention are furthermore obtained bycoupling XI (for example Z=Cl, Br, I, B(OR)₂, SnR₃) with a pyrrolidinoneX, preferably in the presence of catalytically active amounts of apalladium, copper or nickel compound, if appropriate in the presence ofa base, in an organic solvent or a mixture of a solvent with water, atroom temperature or elevated temperatures. Processes for coupling aphenylboronic acid are described, for example, in WO 02/42275.

Suitable palladium catalysts are, in addition to palladium carboxylates,such as palladium(II) acetate, also palladium/phosphine complexes, suchas tetrakistriphenylphosphinepalladium,bistriphenylphosphinepalladium(II) chloride,bis(1,2-diphenylphosphinoethane)palladium(II) chloride,bis(1,3-diphenylphosphinopropane)palladium(II) chloride,bis(1,4-diphenylphosphinobutane)palladium(II) chloride andbis(diphenylphosphino)ferrocenylpalladium(II) chloride. However, it isalso possible to react palladium halides such as palladium(II) chloridein situ with phosphine ligands, giving the catalytically activecomplexes. Suitable phosphine ligands are, for example, arylphosphineswhich are unsubstituted or substituted in the ortho-, meta- orpara-position by halogen, alkyl and/or SO₃H, such as triphenylphosphine,1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane,1,4-bis(diphenylphosphino)butane, bis(diphenylphosphino)ferrocene,hetarylphosphines, such as trifurylphosphine or tripyridylphosphine.

Suitable Ni catalysts are nickel(II) acetylacetonate alone or incombination with the abovementioned phosphine ligands, or Ni(II)acetylacetonate with imidazolium carbene ligands, and also complexes ofnickel(II) salts with the above mentioned phosphine ligands, for examplebis(triphenylphosphine)nickel(II) chloride,[1,3-bis(diphenylphosphino)propane]nickel(II) chloride,[1,4-bis(diphenylphosphino)butane]nickel(II) chloride and[bis(diphenylphosphino)ferrocene]nickel(II) chloride.

Suitable copper compounds are, in particular, copper(I) compounds, suchas CuCl, CuBr and the like.

The catalyst is usually employed in substoichiometric amounts,preferably of 0.001-0.8 equivalents and particularly preferably of 0.01to 0.5 equivalents, based on the pyrrolidinone XI used.

If appropriate, it may be advantageous to convert the compound Xinitially with a base into its salt. Suitable bases are, for example,alkali metal hydrides, such as sodium hydride, and sodium alkoxides,such as sodium methoxide and sodium ethoxide, lithium amides, such aslithium diisopropylamide, and also organolithium compounds, such asbutyllithium and phenyllithium.

The molar ratio of compound XI to compound X is preferably in the rangefrom 0.95:1 to 1:1.5.

Suitable bases are, if required, alkali metal and alkaline earth metalhydroxides, alkali metal (bi)carbonates and alkali metal phosphates,such as NaOH, NaHCO₃, Na₂CO₃, KHCO₃, K₂CO₃, Ba(OH)₂, K₃PO₄, alkalimetal, alkaline earth metal, thallium and transition metal alkoxides,such as sodium ethoxide and thallium ethoxide. Other suitable bases arealkali metal fluorides, such as potassium fluoride, cesium fluoride,ammonium fluorides and tetrabutylammonium fluoride. The base is usuallyemployed in an approximately stoichiometric amount or in up to 10-foldexcess, based on the compound II.

Suitable solvents are organic solvents, such as DMF, dimethylacetamide,toluene, tetrahydrofuran (THF), dioxane and dimethoxyethane. If thecoupling is carried out with boronic acid, the abovementioned solventscan also be employed in a mixture with water, for example in a ratio ofabout 5:1 to 1:5, preferably in a ratio of about 2:1 to 1:2 and inparticular of about 1:1.

The reaction temperature is usually above the melting point and can beup to the boiling point of the solvent. It is preferably in the rangebetween 50 and 150° C.

The pyrrolidino compounds X can be prepared by customary processes, forexample analogously to the procedure described in process A.

C) Alkylation of Compounds of the Formula I in which R¹═H

Compounds of the formula I in which R¹ is hydrogen can be preparedaccording to general methods by treatment with an alkylation agent R¹-Lin compounds of the formula I in which R¹ is not hydrogen. The synthesisroute is shown in Scheme 7.

In Scheme 7, the variables R¹, R^(a), R^(b), R^(c), R^(d), R^(d), R^(e),X, Y, A, n, R¹, R² and R³ are as defined above. L is a nucleophilicallydisplaceable leaving group, such as halogen, for example chlorine,bromine, iodine, or imidazolyl, carboxylate, such as acetate,arylsulfonate or alkylsulfonate, for example mesylate or triflate. Thereaction is usually carried out in the presence of a base. Suitablebases include alkali metal or alkaline earth metal hydroxides, metalhydrides, such as alkali metal hydrides, for example sodium hydride,tertiary alkylamines, such as triethylamine, aromatic amines, such aspyridine, α-, β-, γ-lutidine, lithium diisopropylamide.

Suitable solvents are, for example, chlorinated hydrocarbons, such asmethylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such astoluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyltert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents, suchas acetonitrile, dimethylformamide or dimethyl sulfoxide.

In general, the reaction temperature is in the range from 0° C. to theboiling point of the reaction mixture.

D) Sulfurization of the Compounds of the Formula I in which X or Y isOxygen.

Compounds of the formula I in which X or Y is oxygen can be preparedaccording to general methods by treatment with a sulfurizing agent incompounds of the formula I in which X or Y is sulfur. This synthesisroute is illustrated in Scheme 8.

In Scheme 8, the variables R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X,Y, A, n, R¹, R² and R³ are as defined above. Examples of suitablesulfurizing agents are phosphorus(V) sulfides, organotin sulfides, andalso organophosphorus sulfides (see also J. March, Advanced OrganicSynthesis, 2nd Edition, Wiley Interscience 1985, p. 794 and theliterature cited therein). Particularly suitable sulfurizing agents arephosphorus(V) sulfide and2,4-bis(4-methoxyphenyl)-1,3,2,4-dithia-diphosphetane-2,4-dithione(“Lawesson's reagent”). Sulfurization processes are described, forexample, in WO 95/33718. The reaction can be carried out in a solvent orneat. Suitable solvents are all solvents which are inert under thereaction conditions, for example aromatic hydrocarbons, such as benzene,toluene, xylene, chlorobenzene, basic solvents, such as pyridine,ethers, such as diethyl ether, 1,2-dimethoxyethane or tetrahydrofuran,etc. The temperatures required for the reaction are generally above roomtemperature and in particular in the range of from 50° C. to the boilingpoint of the reaction mixture.

E) Condensation of an Anilide XII

A further route to the compounds I according to the invention is thereaction of an anilide XII with a suitable difunctional compoundL-CH₂—CH₂-L′ with ring closure according to Scheme 9.

In Scheme 9, the variables R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X,Y, A, n, R¹, R² and R³ are as defined above, L is as defined in C) andL′ has the meaning of L.

The cyclization is carried out in the presence of a base. Suitable basesare all bases mentioned under C). In general, the reaction is carriedout in an inert solvent. Suitable solvents are in particular chlorinatedhydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatichydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such asdiethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polaraprotic solvents, such as acetonitrile, dimethylformamide or dimethylsulfoxide. The starting material XII and the difunctional compoundL-CH₂—CH₂-L′ are expediently employed in approximately equimolaramounts; however, to optimize the conversion, it may be advantageous touse an excess of one of the two components. The reaction is generallycarried out at a temperature between room temperature and the boilingpoint of the reaction mixture.

The starting materials XII can be prepared in two steps similarly to theprocess described in Synlett 12 (1969), 1209. In the first step, anisocyanate XIII is reacted with meldrum acid(2,2-dimethyl-1,3-dioxane-4,6-dione). In the second step, the resultingproduct is then reacted with a suitable amine III. In Scheme 10, thevariables R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X, Y, A, n, R¹, R²and R³ are as defined above.

F) CondensationsF.1 Condensation of Anilines IV with tetrahydro-2-furanones XIV

The compounds I according to the invention can be prepared, for example,by condensing anilines IV with tetrahydro-2-furanones XIV according tothe synthesis route shown in Scheme 11. Analogous reactions are known,for example from Tetrahedron Letters, 31 (21) (1990), 2991, and can beapplied to the preparation of the compounds according to the invention.

In Scheme 11, the variables R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X,Y, A, n, R¹, R² and R³ are as defined above. The reaction of theanilines IV is usually carried out in a carboxylic acid, such as aceticacid, at temperatures in the range from 0° C. to 100° C. In general, thestarting materials are employed in equimolar amounts, or one of the twocomponents is employed in excess.

F.2 Condensation of Anilines IV with Carboxylic Acid Derivatives XV andSubsequent Cyclization

The compounds I according to the invention can be prepared, for example,by condensing anilines IV with carboxylic acid derivatives XV accordingto the synthesis route shown in Scheme 12.

In Scheme 12, the variables R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X,Y, A, n, R¹, R² and R³ are as defined above. L is as defined in C) andL′ has the meaning of L. The reaction of the aniline IV with thecarboxylic acid derivative XV is usually carried out in the presence ofa base. Suitable bases are, for example, amines, such as1,5-diazabicyclo[4.3.0]non-5-ene (DBN),1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), pyridine or triethylamine. Thebase is usually employed in up to six-fold excess, based on thecarboxylic acid derivative XV. The reaction is generally carried out ina solvent. Suitable solvents are, for example, chlorinated hydrocarbons,such as methylene chloride, 1,2-dichloroethane, ethers, for exampledialkyl ethers, such as diethyl ether, methyl tert-butyl ether, orcyclic ethers, such as tetrahydrofuran or dioxane, carbonamides, such asdimethylformamide, N-methyllactams, such as N-methylpyrrolidone,nitrites, such as acetonitrile, aromatic hydrocarbons, such as toluene,aromatic amines, such as pyridine, or mixtures of these. In general, thereaction temperature is in a range of from 0° C. to the boiling point ofthe solvent.

G) Reaction of a Pyrrolidinone XVI with an iso(thio)cyanate XVII

Compounds of the formula I can be prepared by reacting pyrrolidinonesXVI with an iso(thio)cyanate XVII in the presence of a base according tothe synthesis route shown in Scheme 13. Such reactions are known, forexample, from U.S. Pat. No. 5,185,349.

In Scheme 13, the variables R^(a), R^(b), R^(c), R^(d), R^(d), R^(e), X,Y and R¹ are as defined above. R³′ has the meanings mentioned for R³which are different from hydrogen. To prepare compounds I where R³═H,preference is given to using the salt of an isocyanate orisothiocyanate, for example sodium iso(thio)cyanate or potassiumiso(thio)cyanate.

Suitable bases include alkali metal hydrides, such as sodium hydride orpotassium hydride, organolithium compounds, such as lithiumdiisopropylamide. In general, the reaction is carried out in a solvent.Suitable solvents include ethers, such as diethyl ether, methyltert-butyl ether, tetrahydrofuran, 1,4-dioxane, anisole, glycol ethers,such as dimethyl glycol ether, hydrocarbons, such as hexane, petroleumether or mixtures of these.

The compounds I and their agriculturally useful salts are suitable—bothas isomer mixtures and in the form of the pure isomers—as herbicides.The herbicidal compositions comprising I permit very good control ofplant growth on uncultivated areas. In crops such as wheat, rice, corn,soybean and cotton, they are effective against broad-leaved weeds andharmful grasses without significantly damaging the crops. This effectoccurs in particular at low application rates.

Depending on the particular application method, the compounds I or theherbicidal compositions comprising them may be used in a further numberof crops for eliminating unwanted plants. Suitable are, for example, thefollowing crops:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napusvar. napus, Brassica napus var. napobrassica, Brassica rapa var.silvestris, Camellia sinensis, Carthamus tinctorius, Caryaillinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffeacanephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucuscarota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypiumhirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypiumvitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare,Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linumusitatissimum, Lycopersicon lycopersicum, Malus spec., Manihotesculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica),Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris,Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica,Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharumofficinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (S.vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum,Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

The compounds I may also be used in crops which are tolerant to theaction of herbicides as a result of breeding, including the use ofgenetic engineering methods.

The compounds I or the herbicidal compositions comprising them can beused, for example, in the form of directly sprayable aqueous solutions,powders, suspensions, including highly concentrated aqueous, oily orother suspensions or dispersions, emulsions, oil dispersions, pastes,dusting agents, broadcasting agents or granules, by spraying,nebulizing, dusting, broadcasting or pouring, or for seed dressing ormixing with the seed. The application forms depend on the intended uses;they should in any case ensure very fine distribution of the activeingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount ofat least one active compound of the formula I and auxiliaries which areusually used in formulating crop protection agents.

Suitable inert auxiliaries are essentially:

mineral oil fractions having a medium to high boiling point, such askerosine and diesel oil, and coal tar oils and oils of vegetable oranimal origin, aliphatic, cyclic and aromatic hydrocarbons, for exampleparaffins, tetrahydronaphthalene, alkylated naphthalenes and derivativesthereof, alkylated benzenes and derivatives thereof, alcohols, such asmethanol, ethanol, propanol, butanol and cyclohexanol, ketones, such ascyclohexanone, and strongly polar solvents, for example amines, such asN-methylpyrrolidone, and water.

Aqueous application forms can be prepared from emulsion concentrates,from suspensions, pastes, wettable powders or water-dispersible granulesby adding water. For the preparation of emulsions, pastes or oildispersions, the 1-phenylpyrrolidin-2-onecarboxamides I, as such ordissolved in an oil or solvent, can be homogenized in water by means ofwetting agents, adherents, dispersants or emulsifiers. However, it isalso possible to prepare concentrates which consist of activeingredient, wetting agent, adherent, dispersant or emulsifier andpossibly solvent or oil, which are suitable for dilution with water.

Suitable surfactants are the alkali metal, alkaline earth metal andammonium salts of aromatic sulfonic acids, e.g. lignin-, phenol-,naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids,alkylsulfonates and alkylarylsulfonates, alkyl sulfates, lauryl ethersulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta-and octadecanols and of fatty alcohol glycol ether; condensates ofsulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene or of naphthalenesulfonic acids with phenoland formaldehyde, polyoxyethylene octylphenol ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenyl polyglycol ether,tributylphenyl polyglycol ether, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylenealkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignosulfite waste liquors and methylcellulose.

Powders, broadcasting agents and dusting agents can be prepared bymixing or milling the active ingredients together with a solid carrier.

Granules, for example coated, impregnated and homogeneous granules, canbe prepared by binding the active ingredients to solid carriers. Solidcarriers are mineral earths, such as silicas, silica gels, silicates,talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite,diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide,milled plastics, fertilizers, such as ammonium sulfate, ammoniumphosphate, ammonium nitrate and ureas, and vegetable products, such asgrain flour, bark meal, wood meal and nutshell meal, cellulosic powdersand other solid carriers.

The concentrations of the active ingredients I in the ready-to-useformulations may be varied within wide ranges. In general, theformulations comprise from about 0.001 to 98, preferably from 0.01 to95, % by weight of at least one active ingredient I. The activeingredients are used in a purity of from 90 to 100%, preferably from 95to 100% (according to the NMR spectrum).

The compounds I according to the invention can be formulated, forexample, as follows:

-   I. 20 parts by weight of a compound I are dissolved in a mixture    which consists of 80 parts by weight of alkylated benzene, 10 parts    by weight of the adduct of from 8 to 10 mol of ethylene oxide with 1    mol of N-monoethanololeamide, 5 parts by weight of the calcium salt    of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct    of 40 mol of ethylene oxide with 1 mol of castor oil. By pouring the    solution into 100,000 parts by weight of water and finely    distributing it therein, an aqueous dispersion which comprises 0.02%    by weight of the active ingredient is obtained.-   II. 20 parts by weight of a compound I are dissolved in a mixture    which consists of 40 parts by weight of cyclohexanone, 30 parts by    weight of isobutanol, 20 parts by weight of the adduct of 7 mol of    ethylene oxide with 1 mol of isooctylphenol and 10 parts by weight    of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil.    By pouring the solution into 100,000 parts by weight of water and    finely distributing it therein, an aqueous dispersion which    comprises 0.02% by weight of the active ingredient is obtained.-   III. 20 parts by weight of a compound I are dissolved in a mixture    which consists of 25 parts by weight of cyclohexanone, 65 parts by    weight of a mineral oil fraction boiling within the range from 210    to 280° C. and 10 parts by weight of the adduct of 40 mol of    ethylene oxide with 1 mol of castor oil. By pouring the solution    into 100,000 parts by weight of water and finely distributing it    therein, an aqueous dispersion which comprises 0.02% by weight of    the active ingredient is obtained.-   IV. 20 parts by weight of a compound I are thoroughly mixed with 3    parts by weight of the sodium salt of    diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the    sodium salt of a lignosulfonic acid obtained from a sulfite waste    liquor and 60 parts by weight of silica gel powder, and the mixture    is milled in a hammer mill. By finely distributing the mixture in    20,000 parts by weight of water, a spray liquor which comprises 0.1%    by weight of the active ingredient is obtained.-   V. 3 parts by weight of a compound I are mixed with 97 parts by    weight of finely divided kaolin. A dusting agent which comprises 3%    by weight of the active ingredient is obtained in this manner.-   VI. 20 parts by weight of a compound I are thoroughly mixed with 2    parts by weight of the calcium salt of dodecylbenzenesulfonic acid,    8 parts by weight of fatty alcohol polyglycol ether, 2 parts by    weight of sodium salt of a phenol/urea/formaldehyde condensate and    68 parts by weight of a paraffinic mineral oil. A stable oily    dispersion is obtained.-   VII. 1 part by weight of a compound I is dissolved in a mixture    which consists of 70 parts by height of cyclohexanone, 20 parts by    weight of ethoxylated isooctylphenol and 10 parts by weight of    ethoxylated castor oil. A stable emulsion concentrate is obtained.-   VIII. 1 part by weight of a compound I is dissolved in a mixture    which consists of 80 parts by weight of cyclohexanone and 20 parts    by weight of Wettol® EM31 (=nonionic emulsifier based on ethoxylated    castor oil; BASF AG). A stable emulsion concentrate is obtained.

The active compounds I or the herbicidal compositions can be applied bythe preemergence or postemergence method. The herbicidal compositions oractive compounds can also be applied by sowing crop seed which has beenpretreated with the herbicidal compositions or active compounds. If theactive ingredients are less well tolerated by certain crops, it ispossible to use application methods in which the herbicidal compositionsare sprayed with the aid of the sprayers in such a way that the leavesof the sensitive crops are as far as possible not affected, while theactive compounds reach the leaves of undesirable plants growingunderneath or the uncovered soil surface (post-directed, lay-by).

The application rates of active compound I are from 0.001 to 3.0,preferably from 0.01 to 1.0, kg/ha of active ingredient (a.i.),depending on the aim of control, the season, the target plants and thestate of growth.

In order to broaden the action spectrum and to achieve synergisticeffects, the compounds I according to the invention may be mixed withmany members of other groups of herbicidal or growth-regulating activeingredients and applied together with them.

Examples of suitable components of the mixture are 1,2,4-thiadiazoles,1,3,4-thiadiazoles, amides, aminophosphoric acid and derivativesthereof, aminotriazoles, anilides, aryloxy-/hetaryloxyalkanoic acids andderivatives thereof, benzoic acid and derivatives thereof,benzothiadiazinones, 2-(hetaroyl/aroyl)-1,3-cyclohexanediones,hetarylarylketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives,carbamates, quinolinecarboxylic acid and derivatives thereof,chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines,dichloropropionic acid and derivatives thereof, dihydrobenzofurans,dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers,dipyridyls, halocarboxylic acids and derivatives thereof, ureas,3-phenyluracils, imidazoles, imidazolinones,N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols,aryloxy- and heteroaryloxyphenoxypropionic esters, phenylacetic acid andderivatives thereof, 2-phenylpropionic acid and derivatives thereof,pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid andderivatives thereof, pyrimidyl ethers, sulfonamides, sulfonylureas,triazines, triazinones, triazolinones, triazolcarboxamides and uracils.

It may also be useful to apply the compounds I together, alone or incombination with other herbicides, also as a mixture with furthercrop-protection agents, for example with pesticides or agents forcontrolling phytopathogenic fungi or bacteria. The miscibility withmineral salt solutions which are used for eliminating nutrient and traceelement deficiencies is also of interest. Nonphytotoxic oils and oilconcentrates can also be added.

The examples below are intended to illustrate the invention withoutlimiting it.

PREPARATION EXAMPLES

The products were characterized by HPLC/MS (high performance liquidchromatography/mass spectrometry), by ¹H-NMR spectroscopy or by theirmelting point.

HPLC column: RP-18 column (Chromolith Speed ROD from Merck KgaA,Germany).

Mobile phase: acetonitrile +0.1% trifluoroacetic acid (TFA)/water +0.1%TFA in a gradient from 5:95 to 95:5 over 5 minutes, at 40° C.

MS: quadrupole electrospray ionization, 80 V (positive mode)

Example 11-(3-trifluoromethyl)phenyl-3-(N-methyl)carboxamido-2-pyrrolidinone

1.1: 1-(3-trifluoromethyl)phenyl-2-pyrrolidinone

54 g (0.34 mol) of 3-trifluoromethylaniline, 110 ml of butyrolactone and5 ml of concentrated hydrochloric acid were heated at reflux for 13hours. Excess butyrolactone was then removed under reduced pressure. Theresulting crystalline residue was washed initially with an aqueoussodium bicarbonate solution and then with water and subsequently withpentane. Drying gave 65.5 g (85% of theory) of1-(3-trifluoromethyl)phenyl-2-pyrrolidinone.

¹H-NMR (270 MHz, CDCl₃) δ (ppm): 7.85 (m, 2H), 7.45 (t, 1H), 7.4 (d,1H), 3.85 (t, 2H), 2.6 (t, 2H), 2.2 (qu, 2H).

1.2: 2-oxo-1-(3-trifluoromethyl)phenyl-3-pyrrolidinecarboxylic acid

Under nitrogen, 50 ml of absolute tetrahydrofuran were added to 13.6 g(0.06 mol) of 1-(3-trifluoromethyl)phenyl-2-pyrrolidinone from 1.1, themixture was cooled to 0° C. and 60 ml of 2M (0.12 mol) lithiumdiisoproylamide in a solvent mixture of heptane, tetrahydrofuran andethylbenzene were added. The reaction mixture was stirred at 0° C. for45 minutes. 5.4 g (0.06 mol) of dimethyl carbonate in 10 ml of absolutetetrahydrofuran were then added. After the addition had ended, thereaction mixture was allowed to warm to 20° C. and stirred for another72 hours. The solvent was evaporated under reduced pressure and methyltert-butyl ether and water were then added to the resulting residue, thephases were separated and the organic phase was extracted twice withwater. The aqueous phase was acidified with hydrochloric acid (10% byweight) to pH=1. The mixture was extracted twice with in each case 100ml of ethyl acetate and the combined organic phase was dried andconcentrated under reduced pressure. This gave 5.61 g (34% of theory) of2-oxo-1-(3-trifluoromethyl)phenyl-3-pyrrolidinecarboxylic acid ofmelting point 121° C.

¹H-NMR (400 MHz, CDCl₃) δ (ppm): 7.9 (s, 1H), 7.8 (d, 1H), 7.5 (t, 1H),7.45 (d, 1H), 4.1-3.9 (m, 2H), 3.7 (t, 1H), 2.55 (m, 2H).

1.3: 1-(3-trifluoromethyl)phenyl-3-(N-methyl)carboxamido-2-pyrrolidinone

0.14 g (1.8 mmol) of a 40% strength aqueous methylamine solution wasadded to 0.5 g (1.8 mmol) of 2-oxo-1-(3-trifluoromethyl)phenyl-3-pyrrolidinecarboxylic acid from 1.2 in 50 ml of dichloromethaneand 0.35 g (2 mmol) of 1,1′-carbonyldiimidazole. The reaction mixturewas stirred at room temperature for 18 hours. The reaction mixture wasextracted with saturated aqueous ammonium chloride solution and theorganic phase was then extracted with water. The organic phase was driedover anhydrous sodium sulfate, the solvent was removed under reducedpressure and the residue that remained was then titrated with methyltert-butyl ether. The insoluble fraction was then separated off, and theresidue was washed with methyl tert-butyl ether. This gave 0.166 g (32%of theory) of the title compound of melting point 128° C.

¹H-NMR (400 MHz, CDCl₃) δ (ppm): 7.9 (s, 1H), 7.75 (d, 1H), 7.5 (t, 1H),7.4 (d, 1H), 7.3-7.2 (br, 1H), 4.0-3.8 (m, 2H), 3.5 (t, 1H), 2.9 (d,3H), 2.75-2.6 (m, 1H), 2.55-2.45 (m, 1H).

Example 21-(3-trifluoromethoxy)phenyl-3-acetyloxy-3-(N-phenyl)carboxamido-2-pyrrolidinone

0.34 g (0.93 mmol) of1-(3-trifluoromethoxy)phenyl-3-(N-phenyl)-carboxamido-2-pyrrolidinone,prepared analogously to Example 1 using the starting material3-trifluoromethoxyaniline, was initially charged in 3 ml of drydimethylformamide (DMF), and 0.04 g (0.093 mmol) of sodium hydride (60%in mineral oil) was added at 20° C. The mixture was then stirred at 20°C. for 30 min, 0.07 g (0.093 mmol) of acetyl chloride was then added andthe mixture was stirred at 20° C. for another 18 h. Water was added andthe mixture was extracted repeatedly with dichloromethane. The combinedorganic phases were washed with water, the solvent was removed and theresidue was chromatographed. This gave 0.27 g of the title compound ofmelting point 140° C.

The compounds of Examples 3 to 191 were prepared in an analogous manner:

TABLE 2

m.p. [° C.] or RT Example (A)_(n) R* R¹ R² R³ (HPLC/MS) 1 — 3-CF₃ Hmethyl H 128 2 — 3-OCF₃ OC(O)CH₃ phenyl H 140 3 — 3-CF₃ H ethyl H 122 4— 3-CF₃ H n-propyl H 112 5 — 3-CF₃ H n-butyl H 111 6 — 3-CF₃ Htert-butyl H oil 7 — 3-CF₃ H cyclopentyl H oil 8 — 3-CF₃ H ethyl ethyloil 9 — 3-CF₃ H methyl n-butyl oil 10 — 3-CF₃ H phenyl H oil 11 — 3-CF₃H CH(CH₃)₂ H 136 12 — 3-CF₃ H cyclohexyl H 141 13 — 3-CF₃ HCH₂-cyclopropyl H 108 14 — 3-CF₃ H cyclopropyl H oil 15 — 3-CF₃ H methylmethyl oil 16 — 3-CF₃ H cyclopropyl methyl oil 17 O 3-CF₃ H t-butyl H122 18 — 3-OCF₃ H methyl H 103 19 — 3-OCF₃ H ethyl H 111 20 — 3-OCF₃ Hn-propyl H 110 21 — 3-OCF₃ H tert-butyl H  89 22 — 3-OCF₃ H cyclopentylH 140 23 — 3-OCF₃ H methyl n-butyl oil 24 — 3-OCF₃ H phenyl H 108 25 —3-OCF₃ H CH(CH₃)₂ H 134 26 — 3-OCF₃ H cyclopropyl H 134 27 — 3-OCF₃ Hmethyl methyl oil 28 — 3-OCF₃ H H H 106 29 O 3-OCF₃ H H H 124 30 —3-OCF₃ OC(O)CH₃ cyclopentyl H oil 31 O 3-OCF₃ H methyl H  98 32 — 3-OCF₃CH₃ tert-butyl H  40 33 O 3-OCF₃ H CH₂-phenyl H 108 34 O 3-OCF₃ H methylmethyl oil 35 O 3-OCF₃ H CH(CH₃)₂ H 123 36 O 3-OCF₃ H CH₂CH═CH₂ H  75 37O 3-OCF₃ H CH₂C(Cl)═CH₂ H  68 38 O 3-OCF₃ H CH₂CH₂CH₂  29 39 O 3-OCF₃ HCH₂CH═CHCH₃ H  87 40 O 3-OCF₃ H CH₂CH═CHCl H  62 41 O 3-OCF₃ H CH₂CH₃ H100 42 O 3-OCF₃ H CH₂CH₂OCH₃ H  85 43 O 3-OCF₃ H cylohexyl H 152 44 O3-OCF₃ H CH₂-cylohexyl H 135 45 — 3-CH(CH₃)₂ H tert-butyl H  51 46 —3-CH(CH₃)₂ CH₃ tert-butyl H  78 47 O 3-CF₃ H tert-butyl H oil 48 O3-OCF₃ H tert-butyl H 112 49 — 2-Cl H tert-butyl H  76 50 — 3-Cl Htert-butyl H 118 51 — 3-Cl; 5-Cl H tert-butyl H 130 52 — 2-Cl; 4-Cl Htert-butyl H  93 53 — 2-F H tert-butyl H 113 54 — 2-CF₃ H tert-butyl H 90 55 — 4-CF₃ H tert-butyl H 155 56 — 2-CH₃ H tert-butyl H  93 57 —3-CH₃ H tert-butyl H  88 58 — 4-CH₃ H tert-butyl H 135 59 — 2-CH(CH₃)₂ Htert-butyl H 104 60 — 3-OCH₃ H tert-butyl H  43 61 — 4-OCH₃ H tert-butylH 132 62 — 2-OCH₃ H tert-butyl H oil 63 — 2-Cl; 6-Cl H tert-butyl H oil64 — 2-Cl; 3-Cl H tert-butyl H oil 65 — 4-Cl H tert-butyl H 155 66 —3-OCH₃ H

H 110-112 67 — 3-OCF₃ H

H 3.78 min,m/z = 405[M + H]⁺ 68 — 3-OCF₃ H

H 4.09 min,m/z = 399[M + H]⁺ 69 — 3-OCF₃ H

H 3.62 min,m/z = 391[M + H]⁺ 70 — 3-OCF₃ H

H 3.89 min,m/z = 397[M + H]⁺ 71 — 3-OCF₃ H

H 4.30 min,m/z = 469[M + H]⁺ 72 — 3-OCF₃ H

H 4.03 min,m/z = 469[M + H]⁺ 73 — 3-OCF₃ H

H 3.95 min,m/z = 443[M + Na]⁺ 74 — 3-OCF₃ H

H 3.93 min,m/z = 443[M + Na]⁺ 75 — 3-OCF₃ H

H 3.61 min,m/z = 525[M + H]⁺ 76 — 3-OCF₃ H

H 3.75 min,m/z = 459[M + Na]⁺ 77 — 3-OCF₃ H

H 3.55 min,m/z = 489[M + Na]⁺ 78 — 3-OCF₃ H

H 3.84 min,m/z = 373[M + H]⁺ 79 — 3-OCF₃ H

H 4.11 min,m/z = 498[M + Na]⁺ 80 — 3-OCF₃ H

H 3.79 min,m/z = 443[M + H]⁺ 81 — 3-OCF₃ H

H 3.88 min,m/z = 373[M + H]⁺ 82 — 3-OCF₃ H

H 3.60 min,m/z = 387[M + H]⁺ 83 — 3-OCF₃ H

H 3.80 min,m/z = 429[M + Na]⁺ 84 — 3-OCF₃ H

H 3.37 min,m/z = 355[M + H]⁺ 85 — 3-OCF₃ H

H 3.17 min,m/z = 356[M + H]⁺ 86 — 3-OCF₃ H

H 4.20 min,m/z = 401[M + H]⁺ 87 — 3-OCF₃ H

H 3.33 min,m/z = 405[M + H]⁺ 88 — 3-OCF₃ H

H 3.52 min,m/z = 435[M + H]⁺ 89 — 3-OCF₃ H

H 3.91 min,m/z = 451[M + H]⁺ 90 — 3-OCF₃ H

H 4.20 min,m/z = 491[M + Na]⁺ 91 — 3-OCF₃ H

H 3.18 min,m/z = 389[M + H]⁺ 92 — 3-OCF₃ H

H 3.85 min,m/z = 460[M + Na]⁺ 93 — 3-OCF₃ H

H 4.03 min,m/z = 475[M + H]⁺ 94 — 3-OCF₃ H

H 3.82 min,m/z = 579[M + Na]⁺ 95 — 3-OCF₃ H

H 3.19 min,m/z = 401[M + H]⁺ 96 — 3-OCF₃ H

H 3.32 min,m/z = 481[M + H]⁺ 97 — 3-OCF₃ H

H 3.75 min,m/z = 383[M + H]⁺ 98 — 3-OCF₃ H

H 4.26 min,m/z = 401[M + H]⁺ 99 — 3-OCF₃ H

H 4.06 min,m/z = 411[M + H]⁺ 100 — 3-OCF₃ H

H 3.54 min,m/z = 415[M + H]⁺ 101 — 3-OCF₃ H

H 3.79 min,m/z = 429[M + H]⁺ 102 — 3-OCF₃ H

H 3.77 min,m/z = 429[M + H]⁺ 103 — 3-OCF₃ H

H 4.09 min,m/z = 435[M + H]⁺ 104 — 3-OCF₃ H

H 3.98 min,m/z = 439[M + H]⁺ 105 — 3-OCF₃ H

H 3.75 min,m/z = 383[M + H]⁺ 106 — 3-OCF₃ H

H 2.93 min,m/z = 421[M + H]⁺ 107 — 3-OCF₃ H

H 3.63 min,m/z = 504[M + H]⁺ 108 — 3-OCHF₂ H phenyl H 104 109 — 3-OCHF₂H

H  80 110 — 3-OCHF₂ H tert-butyl H  64 111 — 3-OCHF₂ H

H oil 112 — 3-OCHF₂ H

H 153 113 — 3-OCHF₂ H

H oil 114 — 3-OCHF₂ H

H oil 115 — 3-OCHF₂ H

H  48 116 — 3-OCHF₂ H

H oil 117 — 3-OCHF₂ H

H  82 118 — 3-OCHF₂ H

H oil 119 — 3-OCHF₂ H CH₃ H  74 120 — 3-OCHF₂ H ethyl H  70 121 —3-OCHF₂ H isopropyl H 126 122 — 3-OCHF₂ H cylopropyl H 130 123 —4-CH═C(Cl)₂ H tert-butyl H 166-167 124 — 3-CF₃; H tert-butyl H 135-1365-CF₃ 125 — 4-SCH₃ H tert-butyl H 166-167 126 — 4-CH(CH₃)₂ H tert-butylH 130-131 127 — 4-OCHF₂ H tert-butyl H 152-153 128 — 3-Cl; H tert-butylH 160-163 4-Cl; 5-Cl 129 — 3-Br; H tert-butyl H 140-141 5-Br 130 —4-NO₂; H tert-butyl H 152-153 5-Cl 131 — 4-OCF₂CF₃ H tert-butyl H 66-67132 — 3-OCF₃ H

H oil 133 — 3-OCF₃ H

H 3.51 min,m/z = 357[M + H]⁺ 134 — 3-OCF₃ H

H 3.67 min,m/z = 359[M + H]⁺ 135 — 3-OCF₃ H

H 2.92 min,m/z = 361[M + H]⁺ 136 — 3-OCF₃ H

H 3.31 min,m/z = 370[M + H]⁺ 137 — 3-OCF₃ H

H 3.23 min,m/z = 370[M + H]⁺ 138 — 3-CF₃; H tert-butyl H 3.65 min 4-Clm/z = 363 [M + H]⁺ 139 — 3-OCH₃; H tert-butyl H 2.87 min 5-OCH₃ m/z =321 [M + H]⁺ 140 — 3-SCH₃ H tert-butyl H 3.14 min m/z = 307 [M + H]⁺ 141— 3-tert- H tert-butyl H 3.62 min butyl m/z = 317 [M + H]⁺ 142 —O—CH(CH₃)₂ H tert-butyl H 3.24 min m/z = 319 [M + H]⁺ 143 — 3-F; Htert-butyl H 3.07 min 4-F m/z = 297 [M + H]⁺ 144 — 3-OCH₃; H tert-butylH 2.64 min 4-OCH₃; m/z = 351 5-OCH₃ [M + H]⁺ 145 — 4-propyl H tert-butylH 3.53 min m/z = 303 [M + H]⁺ 146 — 4-O-tert- H tert-butyl H 3.36 minbutyl m/z = 333 [M + H]⁺ 147 — 3-Cl; H tert-butyl H 3.26 min 4-F m/z =313 [M + H]⁺ 148 — 4-O-propyl H tert-butyl H 3.67 min m/z = 319 [M + H]⁺149 — 4-Br H tert-butyl H 3.19 min m/z = 339 [M + H]⁺ 150 — 4-SCH₂CH₃ Htert-butyl H 3.32 min m/z = 321 [M + H]⁺ 151 — 3-Br; H tert-butyl H 3.49min 4-OCH₃; m/z = 405 5-Cl [M + H]⁺ 152 — 3-Cl; H tert-butyl H 3.58 min4-O-propyl m/z = 353 [M + H]⁺ 153 — 3-F; H tert-butyl H 2.97 min 4-NO₂m/z = 324 [M + H]⁺ 154 — 3-Br; H tert-butyl H 3.86 min 5-Br; m/z = 4524-Cl [M + H]⁺ 155 — 3-ethyl; H tert-butyl H 3.47 min 5-CH₃ m/z = 303[M]⁺ 156 — 3-CH₂; H tert-butyl H 3.22 min 5-CH₃ m/z = 289 [M + H]⁺ 157 —3-Br H tert-butyl H 3.21 min m/z = 341 [M + H]⁺ 158 — 3-ethyl Htert-butyl H 3.23 min m/z = 289 [M + H]⁺ 159 — 3-iso- H tert-butyl H3.46 min propyl; m/z = 333 4-OCH₃ [M + H]⁺ 160 — 3,4- H tert-butyl H2.66 min OCH₂CH₂O— m/z = 319 [M + H]⁺ 161 — 4-CN H tert-butyl H 2.74 minm/z = 286 [M + H]⁺ 162 — 3-CN; H tert-butyl H 2.74 min 4-OCH₃ m/z = 316[M + H]⁺ 163 — 3-CN; H tert-butyl H 2.79 min 4-F m/z = 304 [M + H]⁺ 164— 3-F; H tert-butyl H 3.22 min 4-CH₃ m/z = 293 [M + H]⁺ 165 — 3-CN; Htert-butyl H 3.09 min 4-Cl m/z = 320 [M + H]⁺ 166 — 3-Cl; H tert-butyl H3.53 min 4-Cl m/z = 329 [M]⁺ 167 — 3-CH₃; H tert-butyl H 3.11 min 4-Fm/z = 293 [M + H]⁺ 168 — 3-Cl; H tert-butyl H 3.06 min 4-OCH₃ m/z = 325[M + H]⁺ 169 — 4-heptyl H tert-butyl H 4.50 min m/z = 359 [M + H]⁺ 170 —4-tert- H tert-butyl H 3.73 min butyl m/z = 317 [M + H]⁺ 171 — 4-ethyl Htert-butyl H 3.32 min m/z = 289 [M + H]⁺ 172 — 3-Cl; H tert-butyl H 3.82min 4-iso- m/z = 337 propyl [M + H]⁺ 173 — 3-Cl; H tert-butyl H 3.45 min4-CH₃ m/z = 309 [M]⁺ 174 — 3-F H tert-butyl H 3.96 min m/z = 279 [M +H]⁺ 175 — 3-CH₃; H tert-butyl H 94-96 5-propyl 176 — 3-ethyl; Htert-butyl H 120-122 5-ethyl 177 — 3-O-ethyl H tert-butyl H 86-88 178 —3-OCH₃; H tert-butyl H 150-152 4-Br 179 — 3-OCH₃; H tert-butyl H 137-1394-Cl 180 — 3-Cl; H tert-butyl H 3.86 min 4-SCF₃ m/z = 395 [M + H]⁺ 181 —4-F H tert-butyl H 2.77 min m/z = 278 [M + H]⁺ 182 — 3-OCF₃ H

H 4.16 minm/z = 423[M + H]⁺ 183 — 3-OCF₃ H

H 4.31 minm/z = 469[M + H]⁺ 184 — 3-OCF₃ H

H 3.87 minm/z = 443[M + H]⁺ 185 — 3-OCF₃ H

H 3.76 minm/z = 447[M + Na]⁺ 186 — 3-OCF₃ H

H 3.00 minm/z = 402[M + H]⁺ 187 — 3-OCF₃ H

H 3.75 minm/z = 453[M + Na]⁺ 188 — 3-OCF₃ H

H 3.94 minm/z = 463[M + Na]⁺ 189 — 3-OCF₃ H

H 4.42 minm/z = 553[M + Na]⁺ 190 — 3-OCF₃ H

H 3.85 minm/z = 473[M + Na]⁺ 191 — 3-OCF₃ H

H 4.49 minm/z = 611[M + Na]⁺ *The number in front of the substituentdenotes the position of the substituent on the phenyl ring. ● Attachmentsite RT = retention time, HPLC/MS m.p. = melting point phenyl = C₆H₅

Example 1921-(3-trifluoromethoxy)phenyl-3-(N-(1,1-dimethylethyl))carboxamido-2-pyrrolidinethioneand1-(3-trifluoromethoxy)phenyl-3-(N-(1,1-dimethylethyl))thiocarboxamido-2-pyrrolidinone

0.26 g (0.7 mmol) of1-(3-trifluoromethoxy)phenyl-3-(N-(1,1-di-methylethyl))carboxamido-2-pyrrolidinonewas initially charged in 3 ml of dry toluene, and 0.17 g (0.42 mmol) of2,4-bis(4-methoxy-phenyl)-1,3-dithia-2,4-diphosphetane-2,4-dithione(Lawesson's reagent) was added at 20° C., and the mixture was heated at70° C. for 7 h. The reaction mixture was then washed twice with water.The solvent was removed and the residue was chromatographed on silicagel using a mixture of cyclohexane/ethyl acetate as mobile phase. Afirst fraction gave 0.06 g (22%) of1-(3-trifluoromethoxy)phenyl-3-(N-(1,1-dimethyl-ethyl))thiocarboxamido-2-pyrrolidinoneof melting point 65° C. and 0.08 g (29%) of1-(3-trifluoromethoxy)phenyl-3-(N-(1,1-dimethyl-ethyl))carboxamido-2-pyrrolidinethioneof melting point 116° C.

Use Examples

The herbicidal activity of the 1-phenylpyrrolidon-2-one-3-carboxamidesof the formula I was demonstrated by the following greenhouseexperiments:

The cultivation containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as the substrate. The seeds of thetest plants were sown separately for each species.

For the preemergence treatment, directly after sowing the activecompounds, which had been suspended or emulsified in water, were appliedby means of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subsequently covered withtransparent plastic hoods until the plants had rooted. This cover causesuniform germination of the test plants, unless this was adverselyaffected by the active compounds.

For the postemergence treatment, the test plants were first grown to aheight of 3-15 cm, depending on the plant habit, and only then treatedwith the active compounds which had been suspended or emulsified inwater. The test plants were for this purpose either sown directly andgrown in the same containers, or they were first grown separately asseedlings and transplanted into the test containers a few days prior tothe treatment. The application rate for the pre- and postemergencetreatment was 3.0 kg of a.i./ha.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C.The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least theabove-ground parts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments were of the followingspecies:

Bayer code Common name ABUTH Velvetleaf AVEFA wild Oat LOLMU italienRyegrass SETIT Millet SINAL velvetleaf

At application rates of 3 kg/ha, the compound from Example 3, applied bythe post-emergence method, shows very good herbicidal activity againstAVEFA and SINAL.

At application rates of 3 kg/ha, the compound from Example 18, appliedby the post-emergence method, shows very good herbicidal activityagainst ABUTH, SETIT and SINAL.

At application rates of 3 kg/ha, the compound from Example 18, appliedby the pre-emergence method, shows very good herbicidal activity againstABUTH, SETIT and SINAL.

At application rates of 3 kg/ha, the compound from Example 19, appliedby the pre-emergence method, shows very good herbicidal activity againstABUTH and SINAL.

At application rates of 3 kg/ha, the compound from Example 26, appliedby the post-emergence method, shows very good herbicidal activityagainst AVEFA and SINAL.

At application rates of 3 kg/ha, the compound from Example 26, appliedby the pre-emergence method, shows very good herbicidal activity againstABUTH, LOLMU and SINAL.

1. A compound which is a 1-phenylpyrrolidin-2-one-3-carboxamide of theformula I

where the variables R¹, R², R³, X, Y, A, n, R^(a), R^(b), R^(c), R^(d)and R^(e) are as defined below: R¹ is hydrogen, OH, Cl, Br, C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C(O)R⁴ or OC(O)R⁴; R² isC₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl,C₅-C₈-cycloalkenyl or C₃-C₈-cycloalkyl-C₁-C₄ -alkyl, whereinC₁-C₁₀-alkyl and C₃-C₈-cycloalkyl may be partially or fully halogenatedand/or may carry one or two radicals selected from the group consistingof C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio,unsubstituted or substituted phenyl group, COOR⁵, NR⁶R⁷ and C(O)NR⁸R⁹,and wherein said phenyl group may be unsubstituted or substituted by 1,2 or 3 substituents selected from the group consisting of halogen,nitro, OH, CN, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy,C₁-C₆-alkylthio, C₁-C₄-haloalkylthio, unsubstituted or substitutedphenyl, COOR⁵, NR⁶R⁷and C(O)NR⁸R⁹; is hydrogen, C₁-C₁₀-alkyl,C₃-C₁₀-cycloalkyl, C₀₇-C₁₀-polycycloalkyl, C₃-C₈-alkenyl,C₃-C₁₀-alkynyl, C₅-C₁₀-cycloalkenyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl,phenyl or 3- to 7-membered heterocyclyl, where the 9 last-mentionedgroups may be unsubstituted, partially or fully halogenated and/orsubstituted by 1, 2 or 3 radicals selected from the group consisting ofOH, CN, NO₂, COOH, C₁-C₆-alkyl, C₁ -C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₄-haloalkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylthio,C₁-C₄-haloalkylthio, unsubstituted or substituted phenyl, COOR⁵, NR⁶R⁷,C(O)NR⁸S02R¹³, C(O)NR⁸R⁹ and 3- to 7-membered heterocyclyl, wherein eachheterocyclyl may contain 1, 2 or 3 heteroatoms selected from the groupconsisting of oxygen, nitrogen, sulfur, a group NR¹⁰ and a group SO₂,and, if appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonylgroups as ring members; and/or may contain a ring-fused phenyl ringwhich is unsubstituted or substituted; or R² and R³, together with thegroup N-(A)n to which they are attached, form a saturated 3-to7-membered heterocycle which, in addition to the nitrogen atom, maycontain 1, 2 or a further 3 heteroatoms selected from the groupconsisting of oxygen, nitrogen, sulfur and a group NR¹⁰ and, ifappropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonyl groups asring members; R^(a), R^(b), R^(c), R^(d) and R^(e) independently of oneanother are hydrogen, OH, CN, NO₂, halogen, C₁-C₁₀-alkyl,C₃-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio,C₁-C₄-haloalkylthio, C(O)R⁴, COOR⁵, NR⁶R⁷, C(O)NR⁸R⁹, S(O)₂NR⁸R⁹,S(O)R¹¹, S(O)₂R¹¹ or C₁-C₄-alkoxy-C₁-C₆-alkyl; or two adjacent radicalsR^(a) to R^(e), together with the atoms to which they are attached, forma 5-, 6- or 7-membered saturated or unsaturated ring which may containone or two heteroatoms selected from the group consisting of nitrogen,oxygen, sulfur and a group NR¹⁰ as ring-forming atom and/or may carryone, two, three or four radicals selected from the group consisting ofhalogen and C₁-C₄-alkyl; X, Y independently of one another are oxygen orsulfur; n is 0 or 1; A is 0, S(O)_(k) or NR¹², where k is 0, 1 or 2; R⁴,R⁸, R⁹ independently of one another are hydrogen or C₁-C₄-alkyl; R⁵, R¹¹are C₁-C₄-alkyl; R⁶, R⁷ independently of one another are hydrogen,C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C(O)R⁴, COOR⁵ or S(O)₂R¹¹;R¹⁰, R¹² independently of one another are hydrogen, C₁-C₆-alkyl,C₃-C₆-alkenyl or C₃-C₆-alkynyl; and R¹³ is phenyl which is unsubstitutedor carries 1, 2, 3 or 4 substituents, where the substituents areselected from the group consisting of halogen, nitro, cyano, OH, alkyl,alkoxy, haloalkyl, haloalkoxy, COOR⁵, NR⁶R⁷ and C(O)NR⁸R⁹; or anagriculturally useful salt thereof.
 2. A compound as claimed in claim 1wherein R³ is hydrogen, C₁-C₁₀-alkyl, C₃-C₁₀-cycloalkyl, C₃-C₈-alkenyl,C₃-C₈-alkynyl, C₅-C₁₀-cycloalkenyl, C₃-C₈-cycloalkyl-C₁-C₄-alkyl, phenylor 3-to 7-membered heterocyclyl, where the 8 last-mentioned groups maybe unsubstituted, partially or fully halogenated and/or substituted by1, 2 or 3 radicals selected from the group consisting of OH, CN, NO₂,COOH, C₁-C₆-alkyl, C₁-C6-haloalkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁ -C₆-alkylthio, C₁ -C₄-haloalkylthio,unsubstituted or substituted phenyl, COOR⁵, NR⁶R⁷, and C(O)NR⁸R⁹,wherein each heterocyclyl may contain 1, 2 or 3 heteroatoms selectedfrom the group consisting of oxygen, nitrogen, sulfur and a group NR¹⁰and, if appropriate, 1, 2 or 3 carbonyl groups and/or thiocarbonylgroups as ring members; or R² and R³, together with the group N-(A)n towhich they are attached, form a saturated 3- to 7-membered heterocyclewhich, in addition to the nitrogen atom, may contain 1, 2 or a further 3heteroatoms selected from the group consisting of oxygen, nitrogen,sulfur and a group NR¹⁰ and, if appropriate, 1, 2 or 3 carbonyl groupsand/or thiocarbonyl groups as ring members.
 3. A compound as claimed inclaim 1 wherein R¹ is hydrogen.
 4. A compound as claimed in claim 1wherein R³ is hydrogen or C₁-C₄-alkyl.
 5. A compound as claimed in claim1 wherein R² is C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl,C₃-C₆-alkynyl, C₅-C₆-cycloalkenyl, substituted or unsubstituted phenyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, where C₁-C₆-alkyl and C₃-C₆ cycloalkyl maybe partially or fully halogenated and/or may contain at least oneradical selected from the group consisting of C₁-C₆-alkoxy,C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio, unsubstituted orsubstituted phenyl, COOR⁵, NR⁶R⁷ and C(O)NR⁸R⁹.
 6. A compound as claimedin claim 1 wherein X and Y represent oxygen.
 7. A compound as claimed inclaim 1 wherein n=0.
 8. A compound as claimed in claim 1 wherein theradicals R^(a), R^(b), R^(o), R^(d) and R^(e) are selected from thegroup consisting of hydrogen, halogen, CN, C₁-C₄-alkyl, OCH₃, CF₃, CHF₂,OCF₃ and OCHF₂.
 9. A compound as claimed in claim 1 wherein not morethan 3 of the radicals R^(a), R^(b), R^(c), R^(d) and R^(e) aredifferent from hydrogen.
 10. A compound as claimed in claim 1 wherein 2or 3 of the radicals R^(a), R^(b), R^(c), R^(d) and R^(e) are differentfrom hydrogen.
 11. A compound as claimed in claim 9 wherein the radicalsR^(a) and R^(e) represent hydrogen.
 12. A composition, comprising aherbicidally effective amount of at least compound as claimed in claim1, and at least one inert liquid and/or solid carrier, and, if desired,at least one surfactant.
 13. A method for controlling unwantedvegetation, which comprises allowing a herbicidally effective amount ofat least one compound as claimed in claim 1 to act on plants, theirhabitat or on a seed.
 14. A method for controlling unwanted vegetation,comprising applying to plants, their habitat or to their seed aherbicidally effective amount of at least one compound of claim
 1. 15.The method of claim 14, wherein said compound is applied at anapplication rate of from 0,001 to 3,0 kg/ha.
 16. The method of claim 15,wherein the application rate of said compound is 0,01 to 1,0 kg/ha. 17.A compound of claim 1, wherein n is 1 and A, is oxygen, a group N-R¹²,where R¹²= hydrogen or alkyl, or a group SO₂.
 18. A compound of claim 1,wherein R^(a), R^(b), R^(c), R_(d), R^(e) are independently hydrogen,halogen, CN, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy orC₁-C₄-haloalkoxy.
 19. A compound of claim 1, wherein R¹ is hydrogen, OH,Cl, Br, C₁-C₆-alkyl or OC(O)R⁴.
 20. A compound of formula (Ia)

wherein R^(b), R^(c), R^(d) independently of one another are hydrogen,OH, CN, NO₂, halogen, C₁-C₁₀-alkyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C₁-C₄ -haloalkylthio, C(O)R⁴, COOR⁵,NR⁶R⁷, C(O)NR⁸R⁹, S(O)₂NR⁸R⁹, S(O)R¹¹, S(O)₂R¹¹ or C₁-C₄-alkoxy-C₁-C₆-alkyl; and R² is C₁-C₁₀-alkyl, C₃-C₈-cycloalkyl, C₃-C₈-alkenyl,C₃-C₈-alkynyl, C₅-C₈-cycloalkenyl or C₃-C₈-cycloalkyl-C₁-C₄ -alkyl,wherein C₁-C₁₀-alkyl and C₃-C₈-cycloalkyl may be partially or fullyhalogenated and/or may carry one or two radicals selected from the groupconsisting of C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio,C₁-C₄-haloalkylthio, unsubstituted or substituted phenyl group, COOR⁵,NR⁶R⁷ and C(O)NR⁸R⁹, and wherein said phenyl group may be unsubstitutedor substituted by 1, 2 or 3 substituents selected from the groupconsisting of halogen, nitro, OH, CN, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio, unsubstituted orsubstituted phenyl, COOR⁵, NR⁶R⁷ and C(O)NR⁸R⁹.
 21. A compound asclaimed in claim 1, wherein R² is C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₅-C₆-cycloalkenyl, substituted orunsubstituted phenyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, where C₁-C₆-alkyland C₃-C₆ cycloalkyl may be partially or fully halogenated and/or maycontain at least one radical selected from the group consisting ofC₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio,unsubstituted or substituted phenyl, COOR⁵, NR⁶R⁷ and C(O)NR⁸R⁹; whereinR³ is hydrogen or C₁-C₄-alkyl; and wherein X and Y represent oxygen. 22.A compound as claimed in claim 1, wherein R² is C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₅-C₆-cycloalkenyl,substituted or unsubstituted phenyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, whereC₁-C₆-alkyl and C₃-C₆ cycloalkyl may be partially or fully halogenatedand/or may contain at least one radical selected from the groupconsisting of C₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio,C₁-C₄-haloalkylthio, unsubstituted or substituted phenyl, COOR⁵, NR⁶R⁷and C(O)NR⁸R⁹; wherein R³ is hydrogen or C₁-C₄-alkyl; wherein X and Yrepresent oxygen; and wherein n is
 0. 23. A compound as claimed in claim1, wherein R¹ is hydrogen; wherein R² is C₁-C₆-alkyl, C₃-C₆-cycloalkyl,C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₅-C₆-cycloalkenyl, substituted orunsubstituted phenyl, C₃-C₆-cycloalkyl-C₁-C₄-alkyl, where C₁-C₆-alkyland C₃-C₆ cycloalkyl may be partially or fully halogenated and/or maycontain at least one radical selected from the group consisting ofC₁-C₆-alkoxy, C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio,unsubstituted or substituted phenyl, COOR⁵, NR⁶R⁷ and C(O)NR⁸R⁹; whereinR³ is hydrogen or C₁-C₄-alkyl; and wherein X and Y represent oxygen. 24.A compound as claimed in claim 1, wherein R¹ is hydrogen; wherein R² isC₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl,C₅-C₆-cycloalkenyl, substituted or unsubstituted phenyl,C₃-C₆-cycloalkyl-C₁-C₄-alkyl, where C₁-C₆-alkyl and C₃-C₆ cycloalkyl maybe partially or fully halogenated and/or may contain at least oneradical selected from the group consisting of C₁-C₆-alkoxy,C₁-C₄-haloalkoxy, C₁-C₆-alkylthio, C₁-C₄-haloalkylthio, unsubstituted orsubstituted phenyl, COOR⁵, NR⁶R⁷ and C(O)NR⁸R⁹; wherein R³ is hydrogenor C₁-C₄-alkyl; wherein X and Y represent oxygen; and wherein n is 0.